Frequent Miler on the Air - Drafting the dream: Strategies for drafting the best 3 card, 3 continent dream trip | Ep155 | 6-18-22

Episode Date: June 18, 2022

You're planning a dream trip to 3 continents; which 3 credit cards would you choose for the best combination of welcome bonuses and card benefits? This week, we talk strategy for our upcoming draft -- because once one of us makes a selection, the other two will be left scrambling to strategize the next move. 1:25 Giant Mailbag 2:38 Awards we booked this week Link to the SimplyMiles deal we referenced: https://frequentmiler.com/incredible-the-240x-simplymiles-deal-is-being-honored/ 11:22 Mattress running the numbers: Marriott Homes & Villas stacking deals https://frequentmiler.com/marriott-homes-and-villas-stay-five-nights-get-2x-points-and-free-night-award/ 18:40 Main Event: Drafting the Dream: Strategies for drafting the best 3 card, 3 continent dream trip https://frequentmiler.com/challenge-3-cards-3-continents-buckle-up/ Link to read about the previous 40K to Far Away challenge: https://frequentmiler.com/40k-to-far-away-afterglow-help-us-design-the-next-40kfaraway-challenge/ 51:09 Post Roast https://frequentmiler.com/chase-sapphire-reserve-should-i-keep-it/ 54:21 Question of the Week: Is there a downside to having multiple car reservations and deciding at the counter which update is best? Join our email list: https://frequentmiler.com/subscribe/ Music credit: Annie Yoder

Let's get into the giant mailbag. What crazy thing did City do this week? Time for Mattress Running the Numbers. Ready for the main event? The main event. Frequent Miler on the air starts now. Today's main event, drafting the dream. You know, Nick, we are finally back in business with a big, big team challenge. And that's what we're going to be talking about today. We're going to be doing the best three card, three continent trip that we can come up with. So that means three signup bonuses from three cards. That's our budget. We go as far or build as big, as incredible of a trip as we can dream up with those three signup bonuses.

So that's the challenge that we're going to be talking about today. And we have a fun way of letting us pick the three cards. Anyway, we'll get into that. We're calling that Drafting the Dream, but that's the part about where we pick the cards. So I can't wait. I'm excited. I can't wait either. It's going to be exciting. It's going to be fun. If you enjoyed previous challenges we've done, I think this one is going to be right up your alley too. So we'll talk more about it in a few minutes. But before we get into all that, we are going to talk about the mailbag first, right?

So let's drag out that giant mailbag. Mailbag time. It is. Yeah. All right. So in this week's giant mail, we found a message from, I think it's pronounced maybe Basid on YouTube. Basid says, I was thinking about what new segment could be added to the show. A short segment about some use of points that one of you actually did this week. It would obviously not necessarily be every week, but would be interesting to show some of the real world uses that you guys personally use on a regular basis.

So, you know what? I think that's a great idea. We like that idea. I love it. Nick and I talked about it. We love the idea. We're going to do it. So, you know, we've been every week, we've been doing the what crazy thing segment and the matches running the numbers segment.

And now we're going to slip in when it's relevant, the awards we book segment. And that may take the place of one of the other two. It may be an addition. Well, it'll just be based on what else is going on. Yeah. So I think that's a really terrific idea. I think it's interesting. It's worthwhile. It's worth talking about what we've booked and kind of why we've booked it. So I think that was a great idea. Thank you very much for the suggestion. So let's kick it off, Greg. Have you booked anything interesting this week? Awards we booked this week. Yeah. So I think it was last weekend. Maybe it was Tim who posted

about wide open award availability on Qantas to, you know, between the US and Australia. And I don't know if you remember, not that long ago, there was wide open award availability on United to New Zealand. And I had booked some prospective flights using that award availability. I wasn't thrilled about my return options. So I was good with the outbound, but the return options that I had, I had booked two different return options and figured I would cancel the one I don't use. I didn't really love either one. This gave me an opportunity to book another return, another return option that I like better and on Qantas.

So that'll be really fun. I've never flown Qantas before and fly them business class for, you know, nonstop all the way from Sydney to, I think it is. Oh gosh, Dallas. I think it is, oh gosh, Dallas, I think is the route that I have booked. The other option was LA. And so I can't remember which one, but either way, that's what I did. So I could have used 55,000 Alaska miles, but I instead used 80,000 American Airlines miles. Interesting choice. Why'd you overpay? Right. The reason being that I'm so flush with American Airlines miles because I had bought basically a lot, a lot, a lot of them dirt cheap when there was that Simply Miles deal where

we got something like 260 miles per dollar donating money to Conservation International. Thank you. You're so flush with miles, you decided to flush the miles. So I decided to flush the miles. So the American Airlines miles, because I have so many, are worth less to me than my Alaska Airlines miles. So I just did some quick mental math. I honestly didn't really, you know, those awards were going disappearing fast. So it's not like I wanted to spend a lot of time deciding how to optimize the miles,

just book what I have and go from there. Fair enough. I think that's a good call there. And I think it's worth highlighting the fact that you made that call and why, because that Simply Miles deal, if you looked at it as buying miles, then it was a cost of about three-tenths of a cent per mile, a little more than three-tenths of a cent per mile, right? So if you look at it that way, you're looking at, you spent about $240, assuming you didn't value donating at all, then you spent about $240 one way. That's pretty

good. That's ridiculous. Yeah. I think of it, I remember it was, it came to like 0.4 something. So I just, in my head, I just make it 0.5 just to make the math really easy. So I say it was something less than $400 for me to get for each one-way business class flight. I can tack on, I haven't done it yet, but I can tack on, you know, the extra legs I need to get from New Zealand to Sydney and from Dallas to home for free, you know, because American will let me do that. So I think that's a great value. It really is. And when you look at it from that perspective too, not only like the, okay, American miles are worth less to Greg than Alaska miles are to look at the same question from a slightly different perspective. He paid, you know, we say about $400 for those American airlines miles. And so if he used 55,000 Alaska miles in place of using about $400 worth of miles,

like miles that cost him $400, that would to me be a poor choice because I value those 55,000 Alaska miles more than the $400 spent on the American Airlines miles. So I mean, anyway, you slice, it's the same question, but, uh, but again, it, I think it illustrates why it's worth in that case, having spent the 80, I would have done the same thing and I've been able to ask him miles to have booked it, but I would have, if I were booking that would have done the same thing. So well done, Greg, well done. So how about you? Well, I mean, did you book anything this week? I made a poorer use of miles sort of, but I'll explain. Yes. So I have an upcoming trip to Europe and I'm going to spend a little bit of time in Malta, which I didn't know much about

Malta before, just kind of stumbled on it. My wife was looking at the map of places to go and she's like, what about Malta? So, so I don't know nearly enough about Malta, but I do know that the water looks absolutely gorgeous around Malta and I hate boats, but it looks like the best way to see it is by boat. And you can take like taxi boats, but I got two young kids. And so I was thinking, oh man, waiting in line for a taxi boat here and there to get from place to place. That's going to make it a really long day. It'd be much easier if we could just have our own boat, right? So you can charter boats and I found them first. I just gave it a Google and looked through Viator and things like that. And so you could charter them.

So I went with one that I could book through Ultimate Rewards because I really didn't want to spend the money on it. It was more money than I wanted to spend, but it was not that many, or I shouldn't say not that many, less than 60,000 ultimate rewards points with the Sapphire reserve to charter a large catamaran for eight hours for a full day to have our own captain. It's got a little, I don't know what you call it. I think of a dinghy or I don't know. It's like a little, I can't, they had a name for it, but a little boat on the boat so that that way they can anchor and you can take the little boat to shore if you want. And so that to me seemed like a pretty good deal. I was willing to part with them again, because I generate those miles pretty cheaply, you know,

thanks to all those office supply store deals, it doesn't cost me very much to generate 60,000 ultimate rewards points. So to me, even though it's not a great value, when you look at it, like, oh, I could have booked through buy it or gone through a portal and price matched or use something else, some other tricks to cut the price. And so I could have spent less than the cash price. I'm not really getting exactly one and a half cents per mile, but I'm getting more value than what those miles cost me to make. Well, very good. It's interesting timing too, because I had just posted about how I'm no longer using my ultimate rewards points at one and a half cents each, you know, through the portal or through pay yourself back. But for me, that's not

so much because I don't value that option. Although it's partly that, cause I just have had such bad luck with the portal, but, um, but it's more because I just have been spending my Hyatt points like they're going out of style. And so I don't like the idea of, you know, getting to a point where, oh no, I've spent my ultimate rewards points for one and a half cents each. And now I need Hyatt points that would have been worth, you know, four or five cents each towards this redemption, but I don't have enough points. That would be, that's what I'm trying to avoid. So that's why I'm saving them for that. I mean, that makes a lot of sense. And I certainly see the wisdom in that. And there's frustrations booking through the Chase portal, lots of them. One of them is that they didn't have nearly as many options. There were a lot more options to book through websites like Viator or the various websites where you can book tours. And I'm not

a big Viator fan. You can go to FrequentMiler and search for Viator and find out why. It's just the one that comes to mind because it's like, you know, the one that is most commonly looked at. So anyway, so it's definitely more limited, which is the same problem I've run into with the hotels. And you've talked about that too. So I'm not a huge fan of the chase travel portal, but I am a fan of not having to spend money out of pocket to spend a day like floating around the Mediterranean. So, uh, so hopefully that'll go well. Hopefully I won't get too seasick cause I don't like boats, but Dramamine has worked pretty well for me. So crossing my fingers that my kids are also okay on boats and didn't inherit daddy seasickness. We'll see. Yeah. Yeah. Good luck with that. I I've had great luck with,

luck with, uh, ginger root pills, uh, to combat, uh, seasickness. So you might want to try that too, but I could see why you might not want to risk it. Well, yeah, I mean, I I'm okay with doubling down here probably. Well, you know, I can't hurt. I mean, the worst side effect with ginger root pills are slightly like painful burps. Yeah, I'll deal with that. Because they're kind of spicy burps. That is more convenient than the other types of burps that end up happening. I mean, your wife might not like it.

Right, right. Well, and if you're not familiar with Greg's feeding the fish story, you can go to frequent by order.com and search for feeding the fish. And you can find out why Greg knows a lot about C-sectionists. So a lot about it. Okay. So that was a long, my ginger pills that day. Okay. A long mailbag segment. So we should talk about mattress running the numbers and I'm going to let you set this up. If you're watching on YouTube, I apologize. My video is going to dip out for a second here because I just realized that I didn't plug in my computer. So Greg is going to lay this out while I'm listening in. So this week's mattress running the numbers, Marriott is running a promo for the

homes and villas. Can you explain that for us? All right. Yes. Marriott Homes and Villas. That's the Marriott ability to use points to book basically vacation homes, or you can book vacation homes for cash through Marriott and earn Marriott points. And this promo is for the latter. It's for when you're booking a vacation rental through Marriott and you're earning points. In this case, this promo says, if you stay five or more nights, you'll get double points plus a free night award worth, uh, up to 35,000 points. So, um, you have to book by June 22nd. That's this coming Wednesday for when we're recording. But it's good for stays up to the end of this year. So you can book now, but for a stay that's much later.

And I'll point out that there's been a Chase offer floating around. That's like one of those offers that you can load to your credit card account for a hundred dollars off on a hundred dollars or more spend at a homes and villas. So, so basically you could stack these two, if you have that offer on your chase card and, you know, get not only a vacation rental that you want, but also get double points, a free night certificate and a hundred dollars back. So that seems pretty good. Have you booked one of these yet or what? Like, are you using this?

I haven't booked one yet, but what do you think? Is this mattress run worthy? No, because five nights is going to cost you probably more, even at the cheapest places. It's going to cost you more than the certificate is worth even after you're $100 back. And the points, I think probably, I think it's very unlikely that you're going to find one cheap enough, at least based on my searches. However, if you're in the market for a five-night stay, then it could certainly be a fantastic rebate that comes close anyway to Mattress Runworthy,

I think, because I have found some that are very reasonably priced. In fact, I was looking to use that chase offer. I was visiting family in Myrtle Beach just recently here. And we went to the beach one day. My family lives not right next to the beach. It's like a 20-minute drive or something. And so we were down there with the kids and I looked around and I was like, you know, I said this last time and I forgot about it. I'm going to say it again. We should book a room at one of these hotels down here, just so we got a place to shower the kids off before we toss them back in the car. You know, a place to go in the shade. If somebody needs a nap or whatever else, that would have been really smart because they were very inexpensive the time of year I was there.

So I thought to myself, I need to do that next time. And then I saw this Marriott homes and villas thing. And I was like, Oh, you know what? I wonder if I could use that chase offer and book a place for free. That'd be great. But Marriott had a minimum of three night minimum. So it didn't work out to be good enough deal for that. However, I can say that there were places that were like a hundred dollars a night, or maybe even a little bit less there. I think there were a little less like a hundred dollars a night, or maybe even a little bit less there. I think they were a little less than a hundred dollars a night in Myrtle beach. Now that's obviously a cheap destination, or maybe it's not obvious to everybody, but it is a very inexpensive hotel destination. So that isn't going to be indicative of what you're going to find if you're looking in

New York or LA or something, but depending on where you're going, it's worth taking a look. I think, cause this could work out to be good. I don't think it's probably going to be a mattress run for everybody though. What about you? Yeah, no, I agree. I mean, I do think that Marriott homes and villas are a decent way in general, if you're striving for Marriott elite status to get extra elite nights. And, um, but, you know, I'm not really saying that as far as mattress running, but more, more like, you know, okay, you're looking for a kind of a vacation rental style stay. Um, and you know, this could be a, a, a good, it could be a much cheaper alternative than to booking a hotel for that amount of time. The, the extra awards you're getting with this promo, not that big

to really move the dial much in my mind, but you know, if you're thinking of mattress running at the end of the year to, elite status. I could see where it would make sense to, if you found a cheap stay that you'd likely to want to actually use that's towards the end of the year, to basically say, all right, I'm going to book it now, make a note of the cancellation policy and set a reminder to cancel before whenever the cutoff date is, and then just wait until later in the year and to see, oh, am I close to whatever my elite target is? And if you're still five days away, then maybe you go ahead and complete the stay and that would make sense. It'd be a good way to basically jack up the awards just a little bit over what you would normally get.

Yeah. It's worth mentioning here that you do have to comparison shop a little bit because sometimes, maybe even often, I would say Marriott Homes and Villas will have properties that are also on Airbnb or Vercasa or other vacation rental sites. And often, or at least sometimes, I think often, they're a little bit more expensive booking through Marriott Homes and Villas. So you're probably going to be overpaying a little bit. So you got to do a little bit of math and figure out, okay, does this make sense versus the other options?

But I think that Greg's use is a great one because I've booked those end of year mattress runs just in case I end up needing the nights before. I've done that for months in advance, just like you're saying with hotels, like category one hotels. So this is a really good idea. If you think you might need a vacation rental and you might mattress run, put them together. Don't do them separately, put it together. So yeah, I think that's a, that's the best case scenario for this one, I think. And the one question I have for you that I don't know the answer to, I think the answer is no, but I'm sure somebody is going to ask, is there any way to split tender to be able to use? Because I mean, I have that chase offer on three different cards.

Is there any way to split tender and trigger it on all three cards? Because then that would totally change things, right? Yeah. Well, so as noted in our post about this, sometimes these homes and villas take a, you know, half the charge as a deposit now, and then we'll charge the rest later. So, so in that case, you probably could sort of split tender, but that's relying on that later time still having that chase offer around, which may or may not be the case. Right. So there you go. You know, aside from that, I don't know. Yeah. I haven't tried to call and see if you can book one over the phone know. Yeah. I haven't tried to call and

see if you can book one over the phone and split tender. I wouldn't expect to be able to use multiple cards over the phone, but Hey, I mean, if you found that, if you found that you can let us know, love to hear about. Okay. So for sure that was our mattress running the number segment. So now it's time for this week's main event, the main events drafting the dream. The main event, drafting the dream. So let's talk a little bit about the new challenge. So, you know, two years ago, 40K to far away. Actually, it's a little more than two years ago now, isn't it? It is.

It was 2019. So three years ago, we introduced the 40K to far away challenge, which was where we each had 40,000 points and $400 to go as far away as we could. And that sort of morphed to really build as big of a trip as you could, because we decided not to measure actual miles flown, or at least not to make that the sole criteria of who won. And so we all did like incredible trips. I mean, truly incredible with such a budget. I was talking about it the other day and I was like, just that just sounds unbelievable. Right. So, yeah, we did say you should read the link in the post because that was an amazing trip. It was it was it was amazing. I loved everything about it.

And I think our audience loved it too, for the most part. People were really engaged. And we got a lot of comments, like people saying, at first, I didn't know about this, but it turned out to be really great. But people also had suggestions. And we asked for suggestions for the next challenge. And people came up with really great suggestions. And we had spent a bunch of time talking about those. I mean, like back when they came in in late 2019 and like late 2019 to early 2020,

we were taking those suggestions to heart. We were talking about them. We were fine tuning them. We were planning. We had an idea in mind, a rough like outline that we were pretty close to being ready to announce in January of 2020, when all of a sudden we were kind of like, you know, we were talking about maybe Europe and things are looking a little crazy in Italy. I don't know. And should we hold

off? And, and so of course, you know, if you've been around the last couple of years, you know, you know where that went. It got delayed. It kept getting pushed off. Yeah. So we dug up those old plans and we reviewed them and we made some big changes to what we had thought we were going to do then. were, um, we did in our, in our guck trips, Nick and I did this global upgrade certificate trip and, and I had a whole bunch of challenges for him. And that was like part of our original idea for the, for the next big challenge. And so we kind of did that. So, so we said, all right, well, you know, we've already done that. So let's, let's step back and see, you know, what else makes sense here. And we came up with a pretty creative idea, I think. And so our new challenge is going to be three cards, three continents.

What can you do with three cards and three continents? So, of course, we had to come up with some ideas about how this is all going to work. And three cards, what three cards are you going to pick? And how are we going to decide that? So there were a lot of questions to answer. So our general framework was that each of us competing this time around, it's going to be Greg and me and Steven again. So the three of us are each going to get three credit card welcome bonuses. So we're each going to pick three of them to use to plan the most incredible trip we can. But we're not just going to let all of us choose the same three cards because that would be kind of boring. So instead, we are going to. We're going to do a draft.

We're going to be drafting the dream. So this came directly from a reader suggestion. We changed the details of it, but a reader had suggested a few years ago, why not have a draft style picking so people can pick what awards they get to use for the next challenge. And so we said, all right, let's change that to, we get to draft our credit cards. And so we're going to do a snake draft where we have one player, one contestant picks, is the first to pick. And once they pick a card, that's no longer on the table for the next contestant or the one after and so on. But whatever they pick, the welcome bonus that goes with that is theirs to use for the challenge as well as any perks that that card offers. So a simple example, Chase Sapphire Reserve has $300 travel credit. So if you pick that card,

not only do you get whatever the current welcome welcome bonuses, but you also get $300 of travel spend to use towards a challenge. Very good. So we can use the perks from the cards we pick. So once the first player picks their first card, that card's off the table. And so everybody else gets to pick from all of the other cards on the market. And so you're free to pick whichever cards you want. It's just that each card can only get selected once, just like we were doing a draft for a sports team. So once that card's gone, it's gone. So if Greg takes the Sapphire Reserve with the first pick,

then I'm sitting there looking at, okay, well, which Amex cards are out there and which Chase cards and which City cards, and I have to pick. And the snake draft aspect of it is the idea that, so it'll be player one, player, two player, three in the first round, picking a card. Then the second round player three is going to go first. So player three player two player one. So it'll be a reverse order in the second round of the draft and then reverse again for the third round. So that means the third person to pick, unfortunately has a couple of

cards gone, but then they get to pick two in a row if you're following along with the numbers here so kind of evens it out a little bit and gives everybody a chance to get a couple of good cards and it of course this this system of drafting creates a lot of strategy because you know for example if you go first then your second pick isn't going to be until the sixth pick right so quite a ways away so a number of cards are going to be until the sixth pick, right? So quite a ways away. So a number of cards are going to be gone and you got to plan for some different scenarios. Like what if- That's right. You can't be counting on a really good card for your second pick if you're the first person. But let's talk about, there's two very important constraints that we're putting on

this. First one, first one, you're starting with a cash budget of $1,000. That's it. That's your budget for travel. And the way you expand that budget is by signing up for cards. Well, when you sign up for cards, you have to pay $695 annual fee, that's seven-tenths of your travel budget right there in just getting that one card. Right. Right. So that's a huge sacrifice right off the bat if you pick something like that, because that remaining, if you were to take that card, that remaining $305 has to cover any additional annual fees from other cards that you pick and the award taxes on the flights that you're going to eventually book and hotel accommodations. If there's anything that's not covered by card benefits or hotel points. Right, right. So just for a quick example, if you picked a platinum card first, 695 annual fee, you

can't then pick the Chase Sapphire Reserve or Reserve, which is a $550 card. How much is the Venture X? It's $400. So you couldn't pick that one because you have a $1,000 budget for your first year annual fees and you'd be out of luck. Right. Well, you know, and now that you say that, I guess we got to iron this out because I gave me a question. So if you pick the platinum card first and you wanted to get the Sapphire Reserve, couldn't you cash out some of the points from the Sapphire Reserve to cover the annual fee? No, for cash out points from the Sapphire Reserve? No, no. Because the assumption in my mind is that whatever the, your $1,000 is like your upfront pot of money.

And you can't use- Can't spend it before you- You can't use stuff that you're going to get in the draft in order to contribute to the draft, basically. I see. I see. Okay. All right. That $300 goes towards your travel budget further down. You could use that towards taxes and fees for awards and things like that.

Okay. All right. I see. I see. I figured when we talked about cashback bonuses covering things that those would probably come into play too. But okay. All right. So there you go. You got the rules. Good that I use that example right there. Yeah. Rules decision right there, right off the bat. Okay. So that's one constraint, the thousand dollars, right? So, and, and that's going to cover again, your annual fees, your flight bookings, your hotels, not going to include food. So Steven is not going to be traveling again this time with all of those bags of tuna or whatever it was that he had. I don't remember what he had. Was it tuna or

something? It was something he had in his bags. Yeah. Tuna packets. Yeah. Yeah. Yeah. Steven, go get yourself a bite to eat. No, right, right. Travel and I mean, sorry, food and activities will be separate budgets so that we won't feel constrained to really limit those to close to nothing like we did in the 40K to Far Away Challenge. that that's going to be specifically for travel and things that are necessary for travel, like visas, visa entry fees to get into another country. Okay. So we've got the thousand dollars, but then there's another constraint that we're placing on this because most people don't have an unlimited capacity to spend over the course of a year. And we're kind of trying to imagine this somewhat from the perspective of what could a normal person do? A normal person could sign up for three cards over the course of a year and probably meet the spending requirements as long as they're not outlandish.

So in order to keep it from becoming outlandish, we set a total amount of credit card spend that you can imagine over these three new cards, because we're not probably going to be opening the new cards necessarily because we might already have these cards that we choose to use, right? So we're going to imagine $15,000 in total credit card spend, because that seems like a reasonable amount that most people can handle a little over $1,000 a month over the course of a year. So that seems like it would fit in line with what most people are probably spending at least. So fifteen thousand dollars total spend on welcome bonuses. So if you pick the ink business preferred, for instance, with your first pick that requires fifteen thousand dollars in purchases, then you've got no more spend left for

any of the other minimum spending requirements. I guess you'd be done with a single cart and that'd be it. Right. Right. So that'd be it. Right, right. So that would be a big disincentive to get one of those cards that require $15,000 spend. You could do it and you could, we're going to let people get bonuses on cards that give you the bonus after first purchase, you know, because you could theoretically spend

like a penny or something. So we won't, you know, be that, we'll be that much. Right. Right. We'll let you spend those extra pennies. But, but you'd be really limited because there's not that many cards that offer

bonuses after, after first spend. Right. It'd be, you'd be hard pressed to build a big, impressive trip with the kind of rewards you'd get from that i think but you know someone wants to do it i'd love to see it yeah i mean it could be could be interesting so okay so fifteen thousand dollars in spend now the thing is you can use that fifteen thousand dollars in spend

to meet your welcome bonus requirements and of course whatever required spend you have for the card you're getting we're gonna count those count those points. So, for instance, we brought up the Platinum cards. Got 150,000 point bonus at the time of recording this after $6,000 spend in the first few months. So, we're going to imagine you did the $6,000 spend at 1X. So, in total, you have 156,000 points to use. Now, if after that, the next two cards that you pick both have a $1,000 spending requirement, then you'll have spent $8,000 altogether to meet your welcome bonus spend. You've got another $7,000 spend.

You can choose to put that on whichever of the three cards that you've picked in order to earn a little bit of additional rewards. We're going to imagine you've spent $15,000 altogether and earned the rewards from spending $15,000 at whatever the base earning level on the card is. We're not going to imagine that you hit any category bonuses, just whatever the base levels rewards are on that card. Right. Exactly. So, you know, just for example, if you wanted to spend it on your IHG card, which was one of your picks, IHG card now earns three points per dollar for unbonused spend. So you would get three times. so you'd get 21,000

IHG points with that spend if you chose to use it that way. And you could mix and match if you wanted to. If your plan said, oh, I need 6,000 more IHG points, then spend 2,000 of those dollars on the IHG card and the rest on a different card that gives you better rewards. So there's clearly some strategy there in determining, okay, how am I going to split up $15,000 worth of spending in order to earn three incredible welcome bonuses that cost me less than a thousand dollars to generate, hopefully much less because you're of course going to need some money left over to pay your award taxes and things like that. And so then you can plan the most incredible trip you can to at least three continents. So how do we define going to three continents? Like, I mean, what if I just go to

the town next door to mine? Does that count as a continent? I'm in North America, Craig, does that count? Right? No, we talked about this at length. and what we decided is that North America can count if you go outside of the lower 48 states and you have to do something. Like a layover in the airport does not count as being in Canada, for example. Preston Pysh, But what if I go to like Mexico City and I go to the Centurion Lounge there, Craig? Does that count? Craig Foss, Yeah.

No. You have to at least go out and do something in Mexico City for it to count. All right. So the ultimately, like before, like we did with 40K to Far Away, our readers and listeners are going to be the ones voting to see who won. So if you do something that's not quite, you know, you leave the airport for 10 seconds and say, see, I did it. We're not going to stop you, but it's going to be up to the voters to decide how bad was that or is that good? And I don't think people should be sticklers to the word continent exactly because like, just for example, North Pole is not a continent by any definition I know of. But if you get there, you secure if you, you know, if you get into Santa's workshop using your Wyndham points, I think you deserve to count that as a great continent.

You know, good luck to you. I really hope that happens. It'll make for some great Instagram shots, too. All right. So I agree with you. I agree with you there. And again, we're going to leave the judgment of this whole thing up to readers. We're not going to, we're not going to judge it. We're going to let readers judge just like we did last time. Readers pick the winner. We've had readers pick the winners of all of our challenges so far. We've laid out the rules and what we need to do. And so it's going to be up to the readers to determine, Hey, did,

how did we perform within those constraints? So, all right. So $15,000 spend three credit cards, three continents. And so that's, I think a pretty exciting idea. I mean, do you have some, some things formulating Greg, you've been like searching award availability, plotting out your draft strategy. Only a little bit. I do have some sort of vague ideas. Well, I think we should talk first about who gets to go first and second and third in the draft. So the last big challenge pre-COVID was the 40K to far away challenge. And the winner of the challenge was the one who won the challenge.

You know, I seem to have blocked that out of memory. I can't recall. Anyway, I, Greg, earned the most votes from readers. Thank you, everyone. I should say readers, listeners, viewers. I'm glad he said he earned the most votes from readers. Thank you, everyone. I should say readers, listeners, viewers. I'm glad he said he earned the most votes, not that he won, right? We earned the most votes, right?

I earned the most votes. You know, my wife was clicking away from all the different browsers she could find. And Stephen came in next and Nick came in last. I have to say that it was sort of unfortunate. Third. I came in third, Craig. Third. Third, right. Sounds better. It's better than last. By almost any, anyone's, I don't know, if you could objectively look at the trips and say,

who did the most, who really went the furthest, which was the original description, you know, Nick unquestionably did. But things got murky when he admitted he had gone over budget and then he tried redefining the trip to say, well, he went this far before going over budget. Anyway, it all got murky and I think he lost his votes as a result. Definitely didn't help that I was trying to, you know, pander to something or other. I don't know that i was i was trying to uh you know pander to something or other i don't know i was a typical politician right i was trying to redefine things on the go and and greg planned an incredible trip too i mean like let's not let's not downplay things here greg went all over africa went to the seychelles i mean it's pretty incredible we all had incredible

trips um and and we found out really great things. Like, you know, there were really great award booking strategies and tips that were unearthed because of this. And it made it all worth it. And we're hoping, we're planning, we're going to plan the draft accordingly, which is that the third place contestant from before gets to go first this time. Second place goes second. First place goes third. So that means Nick goes first. Steven goes second. I go third. Then that's the first round of credit card picks. In the second round, I go first. Stephen again goes second. Nick goes third. And then in the third round,

it's flipped again. Nick goes first. Stephen always goes second. And I go third. So with that, Nick asked, what's my strategy for the draft? What have I been thinking about? Pick three and four. Yeah, so I'm in this situation where I look at what the best offers are available, which, by the way, is how we're deciding what we can pick from. It's our own Frequent Milers best offers page. That's our list of what we can pick from. Those are the best offers. Those are the best offers. Those are the best offers. And there's one credit card offer that really stands out above all the others, the 150K platinum card, even though it

has that 695 annual fee, it just dwarfs all the others in so many ways that, you know, that's of course what I would love to get. I'm a hundred percent sure I can't get it. Expect Nick will snatch it up first round. We'll see. I don't know what a strategy is yet. You know, and then you look at, well, what's next best that'll probably be taken by Steven. I don't know. So, so I'm really stuck looking at, okay, of the cards that are good, but unlikely to be picked first round, which is the best for me. But I do have the benefit of, oh, I can also pick the fourth best card on the list. Right. Which is a big benefit at that point. It is. It is a big benefit. I mean, from a planning standpoint, you don't have to worry that somebody else is going to snap something up in

between. Right. So you can exactly two cards that play nicely together. Exactly. I think that that makes a huge difference. And I think that if I didn't, if we weren't doing it snake draft style, like if,

if Nick got to pick first in every round, I would just have such a huge disadvantage that I think it'd be very hard to make this work. But my, all right. So I haven't gotten very far yet in deciding what my trip will be like, where I might go, where I might stay, but I do want to travel in ideally at least business class most of the time. And I do want to, I want lodging to be special. Like I don't want, I'm not, I mean, even though lodging at free couch surfing places was special in the last challenge, I'm not going to do that. What I'm looking for is, is where I could use points in some way to, to have lodging of some sort. And I say it that way, because if I'm sleeping on a cruise ship or,

you know, I'm sleeping on Santa's sleigh, whatever, as long as it's special, as long as I paid with points, um, you know, and got good value from that, that counts. Um, and, but, so I do want that to be special. So my thought is my first two picks ought to, sort of roughly the way I'm thinking about it is my first pick should be a big enough offer with transferable points that I can count on to handle most, if not all of my flights. That's how I'm thinking about it. And that the second pick should be big enough to handle most, if not all of my lodging. The third pick being cash. So what I mean by that is like, just for example, suppose I picked the Schwab platinum card for my first pick

that a hundred thousand point offer. It gives me the ability to cash out points for 1.1 cent each, but I already said, I plan on using most of those points, if not all of them for flights. But later, if I picked, I don't know, the green card with a 50,000 point offer, I could then cash out those points for what's 1.1 times? $550. $550 and use that to pay for like award taxes and fees, use it to pay for airport to hotel transportation, that kind of thing. So there are significant cash costs in a trip like this that I think I need at least one big offer to handle that. Even that, I'm a little unsure that $500, $600, $700, which is the range that most of those offers that can be thought of as cashback. I'm a little skeptical that that'll be enough,

but I haven't done enough planning to really determine. Interesting. Well, so I have done a fair bit of research. I'm not going to call it planning, but a fair bit of research to determine what my options are, because I think Greg makes a really interesting point in that he wants the first card to cover all of his flights and the second card to cover all of his hotels more or less. And, and so I'm in a position where I'm looking at the first pick and then the sixth pick. So, you know, two, three, four, five, there's gonna be four cards gone between you and Steven before I get my second pick. So I know that probably for instance, most of the good ultimate rewards cards are probably going to be gone because I know that Hyatt is really popular. Everybody likes their Hyatt points. So there's a good chance that I'm not going to really have

an option for a good ultimate rewards bonus if I don't take it first, right? I either have to take it first or I got to wait until sixth. And then I'm probably not going to be able to do that. So I have to come up with a different strategy for my next card. And in my case, I'm at least at the moment considering a strategy where I have a card in mind that I don't think you or Steven is likely to even consider. And so that to me is going to be my wild card that I may use in the sixth pick, but I'm going to wait and see what you guys pick because I'm pretty confident that I can hold that one until the ninth pick. And so, so my middle pick may change depending on what else you guys

take. Cause it really does depend on what's what, cause if there's an, you guys don't pick the, you know, whatever the ultimate rewards card that I want, let's say, then I, then I'm going to hop in there, you know, and I'm not sure that the Sapphire reserve is the best answer. And I say the ultimate rewards card. I may yet pick an ultimate rewards card first, just to throw off your strategy. Cause I feel like you and Steven are so likely to want to lean on Hyatt that I almost want to take it away right from the beginning, pick one of them and have, I know Steven will probably pick one. And then Greg is really skating on thin ice trying to pick what, like a Hilton card or something, Greg.

So we'll see. I'm still debating, but in terms of flights, I've already kind of mapped out what I think I'm going to do and which sweet spots I want to cover. And so one of the things that I like about a challenge like this is it kind of fits my style of planning travel. I've said often before that my wife loves to travel, but she hates to fly. And I can't emphasize enough. She really, really hates to fly.

She gets a lot of anxiety over it. I give her a lot of credit because she deals with a lot of anxiety to get on the plane and still does it because she knows that she wants the end result. And she knows the fear is irrational, but it's not that simple. I know. So, so, so because she has that, right, we don't take weekend trips. We're not going to fly somewhere for two days and come back. That's just never going to be a thing. Cause then you get the anxiety leading up to the flight and then you get there and you just got to be anxious about the

flight home. So, you don't get to enjoy anything. So we've always planned trips kind of piecing together other things to make the trip longer. So I always, when I look at an award chart, I'm always scanning the entire chart for where is there a cheap flight? I'm not looking, okay, where can I go from North America? I'm always trying to look for those other connection points. Where is there a cheap spot anywhere? So there were a few things that popped into mind right away that I was like, Ooh, I'd love to try to book this, or I'd love to try to book that. So I had some cool, like connecting things in mind, but man, award availability is looking a little thinner than usual. It's rough. Yeah, it is rough. Yeah. I mean, one mile time wrote about how bad the summer is for award availability, uh, live and Let's Fly mentioned that award availability is scarce

through the end of September. And by the way, we're planning on doing this in September. But we're game. We still think there's awards out there. We're going to find them. We're going to make it work. So I spent some time looking at them. So I mapped out what I think I might be able to do. But of course, between today when we're recording this and when you listen to this and the day we do the draft, which is coming up on Wednesday, the 22nd, since June 22nd, just in a few days, if you're listening to this, when we publish this on Saturday, then you've got just a few days before the draft. So award availability could totally change in the next few days.

Something that I wanted could open up or something that I thought I had in mind could disappear. And so that may affect strategy and planning in terms of how much flexibility am I going to have? And so that's another thing that I really have to consider with my strategy for the first pick and the sixth pick, because whatever I pick first, I probably need to have more than one option because if my desired sixth card is gone, by the time we get to number six, I need to make sure that number one can stand on its own power. Right. So whatever I pick first, I need to make sure is going to be able to book me a pretty incredible trip, even if I can't like, you know, match up. Cause I'm not in Greg's shoes where I can match those two up right next to you. So there's some strategy going into this. So like

I'm already laying stuff out, writing notes, creating a little draft board, like, you know, getting all my strategy in line here. And I imagine that Greg and Steven will too. So that's kind of part of the fun and why we're going to broadcast the draft live because, you know, you've got to be a little pressure, a little timer going. So you have to make your decisions. Oh man, great. Take that card. Ah, I didn't think he was going to take it. Right. And at the expense of revealing something that maybe we'll go back on this decision, but I just want to mention that one cool idea that just came up today in our Slack discussions about this was the idea that we're only allowing, we said we're only allowing cards that are in the best offers page and those offers.

But, you know, I asked about the offers where we sometimes put as an alternate offer saying that you might be able to find through a fresh browser, meaning a private window or an incognito window, you might be able to find a better offer for this card. Are those allowed? So what was it? 130K business gold card, right? Could you go for that? And what we tentatively decided, and I think this would be fun, is that if during the draft, you could share your screen and pull up that offer in a private window, then you can use it. I think so. When it's your turn, obviously. As long as it's listed on our best offers page too, because we do list those types of things

in the alternate offers. And so that's right below the headline if there is another offer. And the reason for this is we can't have something, we can't have a headline saying you're going to get 130,000 points and like somebody clicks through and they don't see the 130

and they're like, oh, what's going on? So we can't have that as a headline offer when we know it's not going to populate every single time somebody clicks on it. We've got to make sure that, you know, whoever clicks on our website, however familiar they are with computers and things is able to see the offer that we've displayed. So that's why these things are under alternate offer because there's things that don't always populate.

But if I think if it's there, if it's under the alternate offer, that's in the information that we provide for readers so that they know what the best offer is and how they might be able to get an even better offer. So I think it's fair game that we can go after those. But like you said, I think you have to be able to show that you were able to get that offer to come up, that it was possible to do. So I'm excited about that. I think that's a good idea for us to include. And it's good information for people out there listening and thinking about these cards, too. I think that adds a fun twist. Yeah. We'll see what happens with that.

Strategy that we have in there. All right. Okay. All right. So I guess that wraps it up. I think so. You know, tune in if you can to the live draft, which will be Wednesday evening. And, you know, go to the blog to see the actual times and everything, time and place.

And we'll have Carrie will be there updating a draft board, like the results of the draft, as we go. Going to be there to be sort of the analyst on the scene talking through each round. Who did what? Why? Why does he think it was a good or bad move? I'm looking forward to hearing his perspective as we go as well. Yeah. Yeah.

I'm very interested in that too. I think it's going to be a lot of fun. And then obviously there'll be posts as we plan our trips and, and, and create our ideas. And we will announce a date when we're ready to do that and ready to travel. So I look forward to all that. That's going to be a good time. And of course, you're going to want to follow us on Instagram if you're not already, because when we do this trip, we are going to be constantly Instagramming things as we go. So if you're not yet following us on Instagram, you should be because that's just the easiest way to post updates throughout the day. We'll obviously have stuff on the blog also.

But if you want to catch stuff in real time as, you know, like Greg is missing his flight and having to rebook something in the last minute. Not that I'm wishing anything like that on Greg, but did finish first last time, guys. Then, you know, you want to watch the Instagram stories. So you want to make sure you're following us there. Absolutely. All right. Now that means it is time for the post roast. Oh, I'm not prepared. All right. Well, I wanted to roast your post about the Sapphire Reserve card, except that I don't really think the card is worth it either. But what I'm going to roast here is that I appreciated the thought you put into the post and the way that you justified keeping it,

even though your travel spend is kind of off the charts this year versus an average year for you, I think. So I think that, yes, it's worth keeping this year because of the travel. I don't necessarily think that makes it worth it long-term, but of course, I know you're going to revisit that in another year. So that's, I think, relevant enough. But the thing that I look at this and say is, OK, but for me, I don't have a justification to keep it other than that.

I write about this stuff and that's the justification. I mean, that's if I want to be able to look up and see, OK, does this show up at one and a half cents per point in the Chase portal, then I need to have the Sapphire Reserve or does this feature of the card work this way? So I think for you and I, the reasons to keep those cards are less analytical sometimes. But at the same time, you made a great argument for why somebody in your position would keep it. And we certainly have readers who do spend that much on travel. So, you know, if you do, then that extra point certainly could make it worthwhile. So I wanted to roast it, but I don't think the card for me, I don't think the card

is worth keeping from a mathematical standpoint. I really just keep it for the convenience of being able to write about it. Yeah. That makes sense. That makes sense. Yeah. Otherwise I'd be a Sapphire preferred all day long. Sapphire preferred.

I think the Sapphire preferred makes much more sense, especially with three X on dining on that card already. And the two X on travel and then a plethora of other cards on the market that bonus travel. I just don't find the Sapphire Reserve compelling enough with the- Right. And again, just to rehash what I sort of concluded in the post, which is as long as I'm spending a lot on travel, the convenience of the best travel protections combined with one of the best rewards for all travel, not specific to airlines or hotels or this or that or the other, but for all travel, getting 3X everywhere for all travel. That combination is a really nice, convenient combination that works well, is

rewarding and makes up for the fact that it does cost a lot for that card. It does. It does. And I use the Ritz card to keep it simple too, to know that the protections are the same all the time. And I'm not spending nearly as much as you are on travel. Otherwise I would be much more concerned about the fact that I'm not earning nearly enough in return for my travel.

But most of my paid travel stuff is just the award taxes. And it's usually not enough that I care that much about the extra point or points for value. Yeah. Okay. I got something caught in my throat. So hopefully I'm going to get this week's question of the week out before I have to cough. No, I'm not going to, I'm gonna have to mute my mic for a second. All right. Nick is, is coughing for those who are listening on the podcast. And now he's drinking from his coffee. I am. I think that was his free spirit cup.

It is. I was intentionally not showing the spirit side. But yes, it is. I was trying not to admit that. All right. So this week's question of the week comes in from Bridget in the mailbag, who's asked a good rental car question that I am not sure about the answer to in today's world, but I know you have rented a bunch of cars. So I was hoping that you'd be able to answer this because you've done quite a bit of travel this year. So Bridget says, is there any downside to having multiple car rental reservations and deciding at the counter, which car to choose based on the upgrades available. We're planning a big ski trip. I currently have two reservations, one for a

midsize and one for a Jeep. The price of the midsize car is half the cost of what the Jeep would be, but I have executive elite status through national. There's no executive aisle at the airport, so it'd be up to the mercy of the counter agent there. Would it be frowned upon to wait and see what they have to offer? And if they can't offer an SUV, canceling that reservation and taking the Jeep reservation instead? Would it be better to book from separate accounts, etc.? So what's the word on booking multiple car rentals? I haven't done that like that. I mean, I have booked multiple where I've booked with two different providers so that in that case, it wasn't really about upgrades. It was about there was a period of time where car rentals availability was really scarce. People were showing up at National or Hertz or wherever, and there were just no cars. So booked two and, and showed up, there was no problem at national. So I just canceled the other one. Um, in, in her example,

I mean, I can't think of a reason why that, that would be a bad idea. The only thing I'd say is when I was booking backups, I did notice that Hertz was starting to impose cancellation fees depending on how you book it. So, you know, don't do it with Hertz or if you do it with Hertz, make sure, you know, that you're booking it in such a way that there are no cancellation fees. And so just whoever you're booking with, just make very, be very careful about that, that there's no cancellation fee, even if it's past the time that you put on the reservation when you cancel. I think that's fine. I don't think car rental companies oversell their rental cars all the time.

So it's not like you're going to be withholding a rental from someone else who needs it by doing that. So I don't think that that is much of a factor if you're worried about that. I think there's potentially some confusion is going to happen if you go show up and you ask about the upgrade and whatnot. I don't know how that'll go for you. So I don't know if people might, you know, a company might be less likely to upgrade you because, oh, well, you already have a, you know, this big SUV also reserved. So let's keep them in the small car. They If you're going to do this through the same rental car agency, then yeah, I would have player one do one reservation and player two the other. But I haven't done two rentals with the same agency.

I've done the same thing as Greg, where I booked a rental with multiple agencies before. And in that case, I think of one time when we were traveling with four adults and a baby. And so I knew we were going to need an SUV or I was hoping for a minivan. And minivans are very frequently on the executive aisles, I find in a lot of national rental car counters. But they were super expensive for the period that I needed. So instead, I booked an SUV with a different rental agency that would accommodate what we needed. I thought the size wise, anyway agency that would accommodate what we needed. I thought the size-wise, anyway, it would accommodate what we needed. And then I booked the midsize car through National, hoping that when I got there, I would see a minivan and the executive aisle and turn if I did. So I just canceled the other one.

So I've done that kind of thing, exactly what you're talking about, plenty of times before. But yeah, my first thought when I read this was, ooh, check those cancellation policies. Because I, too, just like Greg, noticed that Hertz specifically was adding those cancellation fees now for canceling late in the game. So I think you need to be very careful to read the cancellation policy. And Hertz was doing that. But, of course, Hertz owns, what is it, they own budget? Is that what it is? No, Avis owns budget.

What is it? Hertz owns Thrifty. I don't even remember. I think it's what it is, Thrifty. And a lot of these companies, it's one kind of like enterprise, there's enterprise and national and Alamo, really, it's all really one company behind the scenes. So Hertz owns one of them. So anyway, so I would check the details of wherever you're booking, because maybe the other companies owned by the same umbrella agency as Hertz have added similar

terms and we just haven't seen it yet. So I would definitely check the cancellation policy carefully. But otherwise, that's a strategy that I think many of us have used before, particularly, as Greg says, with the scarcity of rental cars last year and the year before. So I think that seems like it's kind of dissipated, right? I mean, I think that it seems to have used up as far as I can tell. Yeah, that much is good news. All right. Best of luck to you, Bridget. Thank you for a good question and one that was worth contemplating for sure. Unfortunately, that means we're at the end for this week. But fortunately, if you enjoyed what we've been talking about and you want to read more about everything we're doing, this three cards, three continents trip and all the other good content we put out all the time, you want to go to frequent miler dot com slash subscribe. Again, that's frequent miler.com slash subscribe to join our email list. You can follow us on all the various social media, YouTube and Twitter and Instagram, et cetera. Wherever you're listening to this show or watching this show, make sure you give us a like, a thumbs up, subscribe, enable notifications so you find out when we post the next episode and be sure to leave us a comment,

feedback, or if you want to send us some feedback or a question, you can send it to mailbag at frequentmiler.com. Bye, everybody.