BiggerPockets Real Estate Podcast - 3 Cash-Flowing Real Estate Deals in 2025 (& Where We Found Them)
Episode Date: May 26, 2025There are still real estate deals even in 2025. To prove it, we’re taking three real (on-market!) deals and analyzing them three ways: as a long, medium, and short-term rental to see which will have... the highest cash flow. All of these properties are around or under the median home price in the US and have at least one strategy that makes them profitable, even in 2025 with today’s high interest rates. To help run the deal analysis, Ashley Kehr from the Real Estate Rookie podcast and Garrett Brown from BiggerStays join us to crunch the numbers. You’re probably thinking, “Short-term rentals always make more than long-term rentals!” but that isn’t exactly the case. With the added expense of short-term rental management, some deals may work MUCH better as a long or medium-term rental. We’ve even got some bonus strategies to share to boost your rental property profits, like renting-by-the-room to get even more revenue and subdividing your lot so you can sell it and pay off your rental faster (more cash flow!). These deals still work in 2025, and today, we’re sharing exactly where we found them. In This Episode We Cover How to analyze a rental property as a short, medium, and long-term rental The one overlooked cost you should ALWAYS account for on a short-term rental A sneaky tactic to get extra cash if you’re on a BIG lot Using the “coliving” (rent-by-the-room) strategy to get even more rent every month Why short-term rental regulations are a good thing for investors And So Much More! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/real-estate-1126 Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
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No matter what anyone else tells you, there are profitable real estate investments available
on the market right now. You just need to know how to find them and how to implement the right
business plan to maximize your returns. Depending on the property and the market, that might
mean a short-term rental strategy or a long-term one. Today, we'll show you how to project
expenses, revenue, and other key metrics for either strategy. Select the best one to achieve your
goals and put yourself on the path to financial freedom.
Hey, everyone, it's Ashley Care, guest hosting the Bigger Pockets Real Estate
podcast for Dave Meyer today. I have Garrett Brown here with me, Bigger Pocket short-term
rental expert and host of the brand new Bigger Stays YouTube channel. Garrett, how are you?
I'm doing great. I am super excited to be back talking deals with you, Ashley, and it's one of my
favorite things to do anytime. We have a really fun show lined up for you guys today. I gave
Garrett's some homework and he brought three real on market deals with him. They're in three different
locations and at three different price points. We'll analyze each one as both a short-term rental
and as a long-term rental so you can see the pros and cons of each strategy. Along the way,
we'll share a few key methods we use to break down deals that you might be missing in your
own property analysis. Okay, Garrett, are you ready? Born ready. Okay, so Garrett, what is the first deal
that you brought us today to analyze. So the first deal is in Fredericksburg, Texas, which this
city rings bells with anybody within Texas of a travel destination here, but maybe not for other people.
This is one of the highest performing short-term rental markets in the country, but it's also about
30 minutes away from Austin, Texas, and it's its own booming metropolis in many ways. It has many
wineries. It's like a really cool tourist destination for a lot of people, but it's grown in just
general size in the last few years. So there's a three-bedroom two-bath property that has been on the
market for a good bit that I've had my eye on. It's about 1,800 square feet, and it's priced at about
449,000 right now. But when I analyze it as a short-term rental, it can project the revenue of
being almost $74,000, which was the shocking part about that is that's actually one of the lower
projected revenues in the neighborhood that it's in. There's a few of them that are performing with
$120,000 a year revenue, $100,000 a year revenue.
But the secret sauce for short-term rentals is the purchase price, I don't want to say it's
irrelevant with short-term rentals, but the thing that really pushes the needle and how you
can get up to that $100,000, $120,000 gross revenue, mind you, per year is the amenities
that you add and then being able to get your average daily rate and your occupancy goals up.
AirDNA, they're kind of the short-term rental data expert for a lack of better.
words within the industry and their projections are it's going to have a 40% occupancy rate with a
$437 average daily rate, which is what you could bring in as a short-term rental. But the key
with AirDNA, and they'll tell you this themselves, is that's just a baseline number. You want to go in
and really analyze your competition and comparables that are nearby. And after I did that,
using AirDNA and tools like Airbnb, I see that something as simple as adding a hot tub and making
the backyard just, you know, a little nicer and welcoming. That's how you could probably get to that
100,000, 120,000 revenue side that we're kind of looking for. Because my current cash on cash
projection, if we just use the baseline air DNA numbers, is pretty low. It's close to about 1%, which is,
you know, I would never say anybody to do that deal. But where the true short-term rental investors
and the ones that have been winning in some markets is they go in and to analyze these and actually
you're able to beat the air DNA projections quite a bit if you're able to analyze your competition
and see what they are doing so well that is getting them to that top of the market to reach
that, you know, 100,000, 120,000 that we're hoping for. If we add a few simple amenities and
keep our renovation costs and furnishings in line, we should be able to get it up to closer to
about 15%. Well, first I want to point out how you're taking into account the operational piece.
So you're looking at the numbers of this.
property. And like on the rookie podcast, we constantly stress like, what do the numbers say?
Like, stick to the numbers. Don't get emotional bought a property. But I think the difference
between a long-term rental and short-term rental is that you have that hospitality piece,
that operational piece, where you are able to almost manipulate the numbers in a different
sense because of that operational piece where as long-term rentals, like, yes, you can have a
better performing property because it has nicer amenities or your, you know, better property
manager, people will pay more to stay there. Whatever that may be, that's, it's not going to move
the needle that much. Like you have to stick to your projected rents where in your case,
you can manipulate to actually make the deal work for you based on the operations. And I think that's
a really, really unique like strategy. And what is your advice on if you're a rookie investor going to
buy your short-term rentals. Should you bank on that or should you wait until you get some experience
under your belt before you're tying in that operational piece into your deal analysis?
I always tell people that are potential investors and things to analyze it from a short-term
rental side with the operations from day one, but then also make sure if you're newer to this
and you're not 100% certain on a market or different things, or even if short-term rentals
are the strategy you want to go after. You want to make sure that it can also,
possibly work as a long-term rental or even a mid-term rental because you want a few different
exit strategies, especially when you're newer to this type of investing. There's a lot to it that
you may not expect. And so if this is a strategy that's brand new to you, I think when you're
looking at some of these type of deals, analyzing it from the mid-term rental and the long-term rental
side is going to be extremely invaluable so that you can pivot if it's ever needed.
That's a great point to have those exit strategies in place. And one thing,
I think that I want to make clear, too, is that when I say Garrett takes into that operational
piece and how he can make the property unique, he's still looking at the numbers. He's just looking
at the higher end because he's going to be able to get more. It's not that he's completely
winging it and saying, oh, my, you know, unique skill is worth $200 more at night. It's still looking
at the numbers. But instead of taking, you know, what the median rent is or the average rent of the
property. You know, he's going towards a higher end of the better performing properties because he
knows he can get it there. You know, like I said, this is projected about 74,000. I'm very confident
that I can beat that number because there's proven comps within a, you know, a few block radius
four or five that are doing 90,000, 100,000, 110,000. So that's how I have the confidence that I
can get to there. But if you didn't see the comparables that are showing that, your chances of just
adding a few amenities and hitting that number start to dwindle down. So you just, you just,
need to look at it from all perspectives and make sure there are comps that can support what you're
planning on trying to do. Well, I wish I was as confident as Garrett that I could make this work
as a long-term rental. But looking over this deal, so the first thing I did, I went to the
BiggerPockets.com slash rent estimator. And I put in the property address. I put in the bed,
bath count and it's telling me the median rent is $2,490 per month, okay? On the low level,
1,200 to the high level, 3200. So that's kind of a wide margin, but the majority, it kind of shows
to the graph of where each of these places are very, very small amount are in that high 3,200.
Maybe if you went in and did an extensive rehab on this property, you could get that to the high end,
but then we're just adding more and more money that we need to put into this deal and refinance autumn.
So then I went and I did what would I estimate the mortgage payment to be?
So I just did general 20% down 30-year fix at a 6.63% rate, which honestly, if you're going to use this for an investment property, it's probably going to be higher.
But that came out to be $2,200 a month just for the principal and interest.
and then taxes ended up being 378 per month, home insurance, about 150.
And that's just kind of going off an estimate.
So this deal does not pencil out because already your monthly payments, not including
anything else besides taxes, insurance, principal, and interest is going to be about
$2,800 on the lower end.
You might have an higher interest rate that increases that, or higher insurance because
insurance rates are increasing.
So I'm going to do thumbs down, no, this would not work as a long-term rental.
I can agree with that.
This is definitely a very, if you're a short-term rental investor that has a little experience,
it's a great market for you.
Otherwise, I think there's a better option coming in deal three that I think might
be a little more appetizing for long-term renters.
Okay.
Well, we're heading across the country from Texas to the Pacific Northwest for Garrett's next deal.
But first, we must take a quick break.
We'll be right back.
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Okay, Garrett, tell us about deal number two. We're in the Pacific Northwest right now.
What area is this in? So this is in Wheeler, Oregon market. I have never invested into the
Pacific Northwest, but I've always just been completely enamored with the beauty of the, of nature
they have out there, the amount of national parks, state parks, and the vast amount of tourism
they have that is driving out there. So this is a new market and area that I've been exploring some.
They have a tremendous amount of tourism that comes in there. It's about 3-2, it's about 1,300 square feet.
But one of the coolest thing, and when you're thinking from a short-term rental perspective,
which my brain always goes there, especially now that I've been doing this for so long in the short-term rental side,
this has a really immaculate ocean view and mountain view.
If there's a view, your chances of becoming a successful short-term realm,
when I say a view like a spectacular view, this shoot through the roof.
And so this has that wow factor to me, and it's in a great area that has very high occupancy
and can achieve very high average daily rates.
And there's even an opportunity that you might be able to maybe place a tiny home unit
or an ADU unit on side of it, you know, looking into the permitting and what the deed
restrictions are in that area. It's going for about 339,000. It's been on the market for a little bit.
So you never know there might be some wiggle room there. It's projected to have revenue of about
$65,000 annually per year. The occupancy rates are pretty good. They're about 55% according to
AirDNA. The average daily rate's pretty good. It's about $330 according to AirDNA as well.
the cash on cash projection for this property is not significantly high, just using the baseline
numbers from AirDNA. It's about 4%. And I'm not as confident as I am with the Fredericksburg
market by looking at some of the comparables that I can add some amenities, do some extra things to get
it to maybe $100,000 a year like I was in the Fredericksburg market, because the nearby comparables
are making about the same that AirDNA already projected. It's one of those things where you could
add a hot tub, I'm sure, and probably get your amenities and occupancy up. My goal would be to get it to
12% cash on cash return, but I'm not as confident in this market based on what I'm seeing with the
comparables nearby. So if we're able to negotiate the property price down and maybe get some
seller credits, then I might be able to help the cash on cash return, but those don't move the needle
too much in short-term rentals. Getting your occupancy up and your average daily rate is really how
you maximize your cash on cash return specifically for short-term rentals. And I'm not as confident
in this area now. So I've been looking at this deal just because of the view and being able to
probably be the highest performing in the market, but I'm a little worried that I'll still never be
able to hit the exact revenue goals that I'm hoping for what it takes with the operation side, too,
of hospitality and short-term rentals. What are you kind of seeing from what you're looking into on
the long-term side and everything else? Yeah. So the first thing about the,
the negotiation piece if you have a great agent is it's already been on the market for 58 days.
So maybe there is a little wiggle room there.
But I did the same thing.
I did the last one.
I put it into the rent estimator.
It's at $1,100 per a month on the low end, $7.96.
And then kind of on the high end was $1,300.
And then it was very weird, but there was two properties that were actually getting over $3,000 a month.
So those, I don't know if they were listed as like.
fully furnished or what, but that I think kind of skewed the data a little bit. So we're going to
take $1,100 per month for this property. Then we're going to go look at, you know, what the mortgage
payment would be on this property. So I did kind of the same rules. I did last time the mortgage
payment ended up being about $2,000 per month with property taxes and insurance included. So already
this doesn't pencil out. You're looking at about, you know, a $900.
to sit in cash flow every single month.
But there was something that piqued my interest and could make this deal work.
So in the listing, it mentions that you could potentially divide the lot.
It's 100 by 100 lot.
And you could build an additional structure.
But what I think that you could do with this, go to the planning board.
You'd ask for that, you know, the parcel to be divided, parceled off into its own
separate piece.
and I would sell that lot, especially as a long-term rental, I don't need a big lot.
You can maybe get a little bit more in rent.
I mean, this definitely is market-dependent.
And I'd have to look into more of what people expect when they're renting.
But like, the bigger the lot, the more you have to maintain as the landlord.
Even if you tell the residents their job to maintain it, it doesn't mean they're always going to, you know, trim the bushes, cut the grass leg, do all these things to take care of a bigger lot.
So I see the opportunity to parcel this lot and list it for sale, sell that, let somebody else build their own structure on that, but use the cash from that to offset some of the costs of this property and that could bring your monthly payment down and that could actually make the deal work too.
You also could combine strategies too.
I have a property that one of my most successful ones is a piece of land that I divided some and I have a long term rental on it and a short term.
rental and the long-term rental tenant, which you have to find the right person and, you know,
there's a my myriad of things that come up. They actually help me run some of my short-term
rents and they also rent from me for my, for the long-term rental. And I give them a little bit
of a discounted rate and we work out, you know, some payment things on like a 1099. But you also can
mix strategies as well and possibly find something that can work for a little bit of both,
especially if you're able to split the lot and and get added value on both sides, there's a
myriad of ways within real estate that you can be creative and make a deal work to its highest
and fullest potential and balance out the risk and rewards.
Well, we have one more deal to share today, which is at an even lower price point.
It's well under $300,000.
But first, we're going to take our last break.
We'll be right back in a few minutes.
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contributing right now. Your side room wants a side hustle. Even your Wi-Fi is like,
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of sending your income upwards.
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Okay, welcome back from our short break, and we are here with Garrett, who has brought us a couple deals today, and we're going to be talking about the third one now. So where is the third deal today, Garrett?
This is in Waco, Texas, which I'm not sure if we have any Chip and Joanna Gaines fans listening.
I was just going to ask is that from Mr. Ruppert.
Yes, that is absolutely. So it kind of blows my mind, like, and I'm a native Texan for a long time, like how popular Waco has become in the last, you know, maybe 10.
years and a lot of it is solely dedicated to Chip and Joanna Gaines. They have built like an
amazing infrastructure out there. That's, you know, that's where all the fixer upper episodes
were filmed for most of them. So it's become a pretty popular destination because they've added
a lot of other things to. They have some really cool tourist destination like these old silos that
people go tour. There's a lot of, it's kind of hustling bustling. It's near all the major
metro hubs of Dallas, Austin, and Houston. It's kind of like a midway point for all.
them. So it's become a pretty popular short-term rental market, but it also has a lot of real
estate metrics overall that make it a great area in general from long-term to mid-term rentals.
And I've had my eye in this area for a while. This property is a three-tooth. It's about
1,400 square feet. One thing I really like about this property is that it comes furnished.
You spend a lot of money up front, you know, when you're furnishing a short-term rental and
I did a breakdown on BiggerStay's YouTube channel talking about how much it actually costs to
start a short-term rental business, one that you own. And one of the biggest price differences
that comes in is when you have to furnish it yourself. Because if you get into a property that already
has furniture, the cash you're having to put out immediately is almost cut in half sometimes,
depending on how the price point, something like this, it's going to be close to that. So it's listed
at about 275. This is not a vacation destination only area. You know, like the other two that we
kind of mentioned first, those were definitely more tourist vacation areas predominantly.
This one has metrics all around.
The occupancy is pretty good.
It's about 52% according to AirDNA.
The average daily rate is around $220.
So they're a little bit on the lower end, but there's not much renovation that you need to put into.
And there's not much furniture that you need to put into it, maybe $10,000 each for both of them.
The issue here that I want people to pay attention to for when you're getting into this type of market that may not fully be a vacation destination area is Waco has started to.
crack down on the amount of short-term rentals that are able to get permits in the area.
I was able to look at the city code, look at their short-term rental restrictions and different
compliances they put together. They're usually available online. A simple Google search can at least
find most of it to type in, you know, Waco short-term rental regulations. This property sits on
a street that you're able to do short-term rentals on. So I'm looking at the competition nearby.
There's a few of them that have gotten to 52,000. There's two of them that one does a
60,000, another one does 65,000 gross revenue annually. So I at least know there's a little
upside compared to what AirDNA is projecting at the 42,000. When I'm looking at a short-term rental,
I really want to see if the backyard has room for improvement. There's usually two reasons why
people will book short-term rentals over a hotel, especially in this type of area. If you have a
really cool backyard that has the amenities that cannot be provided privately at a hotel, and if you
have a stellar kitchen. You know, that's the one thing I always tell people is your kitchen. You need to have
all the utensils and it needs to be nice because this is one selling point versus somebody going book
a hotel with their family is that you have the kitchen and backyard. If you look at the cash on cash
return for this type of project, though, it is definitely nothing that I would personally want to
get into for this exact property from a short-term rental side because even with the furniture in it
and not having to spend much on it, you're going to be looking at probably a negative 15% cash
on cash return, which immediately turns you off. And my brain was like, okay, maybe I can get to that
$60,000 to $65,000 annually that a few properties are doing nearby as well. But even if I got
close to what they were doing, I'm still probably at around a 4% or 5% cash on cash return. So I started
to pivot and think like, okay, if I was going to really go into this deal because I do love the Waco
market and I think this is a great property for, you know, numerous different reasons. This would be one
that I might possibly look into the midterm rental side because there's a lot of hospitals over there,
you know, between all of the chip and Jana Gaines dynamics that they're bringing in over there,
there's actually a pretty high influx of midterm renters going into this market looking for furnished
properties. And I think that I could probably cash flow as a midterm rental, which is a lot less on
the operation side than it is a short term rental. Something in the,
you know, maybe this is just cash flow after, you know, mortgage and other things are taken out.
We probably could get in between 3 to 4,000 per month.
And so I'm sure you probably have been analyzing to see what it looks like as a long-term
rental.
So I'd be curious what your thoughts are between some of the different, you know, short-term, mid-term
rental ideas I had or if you think this is maybe a better long-term rental play.
Yeah, I actually, after you mentioned the mid-term rental, I went to Furnish Finder.
And I looked in here what it would be.
And it looks like just for a two bedroom is going for around 2,200 per a month.
So I think you could get a very decent rate with a three bedroom here for a midterm rental.
On the long-term rental side, I went again to the rent estimator.
It says about 1,600 per a month.
But it's pretty, like, confident in its score.
Like, it's showing that there's quite a few properties that are in that kind of realm.
There's one that's, like, price super high at 2,300.
And then the lowest is about 1,100.
When you go to kind of the monthly payment on this property, you're looking about $2,100.
So, you know, just comparing those two numbers, they don't work.
But I did see in the listing that it is located near a university.
So maybe there is that option for midterm rental, you know, if you have adjunct professors coming in or something like that.
But I did think, too, that I believe that.
2025, the hottest strategy is co-living. You know, short-term rentals were for a while, glamping was,
midterm rentals were. And I think this is the year that co-living. So this is a pretty nice property.
One thing that I would have liked to see is this kind of has an open floor plan where there's a
huge opportunity to take a single family home and turn like, if it has a separate dining room,
turn the dining room into another bedroom. Yep. I did. I did. I,
even mentioned that Waco is, you know, home of Baylor University, which is a major university within
Texas. So the midterm rental market and co-living, like, I think those could be great, you know,
options to explore in this. And it's been on the market for a good bit too as well. So this is
another one working with a highly qualified agent through, you know, the bigger pockets agent finder.
You will probably have a lot of leverage to work on that negotiation, the purchase price or
do seller credits, you know. And so there's a lot of options when something
has been stale for a little bit.
And, you know, coming furnished actually might work in your favor because that might not
be as appealing to other people looking to properly buy this property.
Yeah, 245 days spent on market.
Like, doesn't that automatically make you think, like, what's wrong with it?
And it could be nothing.
It could be nothing wrong with it.
You'll be shocked sometimes.
Like, I make, you know, luckily I'm an agent and so I can always make offers on properties
I like and not feel bad of making my age, like, oh, make low ball efforts.
you know, but you'll be shocked at some of the offers I'll put out there sometimes and they'll
entertain it. Like maybe they're finally getting to that point now where they're like, all right,
I'm at my wits end. Like, let's see if somebody has a deal for me. So there's nothing wrong with
working with a good agent, setting that standard with them and telling them like, I'm going to
buy something. I might lowball a few. Like, you know, don't hate me for that. And you know,
most agents, if they're an investor-friendly agent that like the ones that come from bigger pockets,
agent finder, they're going to fully understand that strategy and also help you really understand
in that market. You know, list prices are just a suggestion. So, you know, you give your
suggestion for what you think it's worth and stick to your numbers. If you have a number,
once you do your deal analysis, that you're like, I like this property, but I would only buy it
at 235. Don't get emotional. Don't go above that, you know, and go to the next one and get your
repetitions in. And this will start to slowly work your investing memory muscle. And then you'll
eventually be able to knock a few of those deals out the park. And a few of them will start going
your way. It's a numbers game sometimes. You'll be way more emotional with a property when it
performs really well and cash flows great than if you just liked it when you walked through for the
showing. Yeah, yeah, absolutely. You'll be way more emotional if you buy the wrong deal. So that's why
stick to your numbers. Well, Garrett, thank you so much for bringing those deals on today and for
sharing with us. Thanks to everyone for listening to the show today. I'll see you over on the real estate
rookie channel and you can find Garrett on his new channel, BiggerStays on YouTube.
Dave Meyer will be back soon with another episode of the Bigger Pockets Real Estate
Podcasts in a few days. Thanks for watching. Thank you all for listening to the Bigger Pockets
Real Estate podcast. Make sure you get all our new episodes by subscribing on YouTube, Apple,
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I'm the host and executive producer of the show, Dave Meyer. The show is produced by Ian K. Copywriting
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