The Landlord Lens - How AI is Transforming Property Management

Episode Date: May 8, 2026

AI is changing how landlords manage properties, communicate with tenants, review leases, handle maintenance, and save time on repetitive admin work. In this episode, Ava from TurboTenant sits down with real estate investor Ashley Kehr to talk about how she’s using AI in her rental business and where landlords still need to be careful.Ashley shares practical ways landlords can use tools like ChatGPT, Claude, and TurboTenant, while also explaining why human oversight still matters for legal compliance, fair housing, and tenant communication.Connect with Ashley:Instagram: @wealthfromrentalsYouTube: @wealthfromrentals

Now that it's gotten to the point where it can actually take over your computer and build you things, I think every entrepreneur should be using it in their business. Hi, everybody. Ava here with TurboTenet, the partnership in events manager, subbing in again for Seamus and John. They're hitting the slopes right now, but they'll be back soon. And I'm really excited because we're here with Ashley Care, who doesn't really need. an intro on our channel. Ashley's been in real estate for 13 years and done over 60 deals. She's also co-authored the Bigger Pockets Book Real Estate Rookie. And welcome to Denver, Ashley. Thank you so much for having me. And we have a really great topic today, of course. AI, obviously controversial. Some people love it. Some people want nothing to do with it. And some people are somewhere in the middle. But regardless of where you stand, it's already changing the way businesses operate. I'm curious, Ashley, how often do you personally use it in your day-to-day?

Yeah, so I started out with chat GPT and just basically I used it as a Google. I used it as a search engine to start, but now I've really learned the inner workings of what it can do. So right now I'm trying to train AI to be my assistant. So one thing I was actually working on on the plane right here is I have a virtual mailbox. So all of my mail gets sent to a location. they scan it all in for me and I view it online and then I file it and then I pay it or whatever. So I'm trying to train the AI to actually view that mail for me, sort it for me, and file it. And just so I don't even have to look at it. So that's something I'm working on right now.

And then just short-term rentals, long-term rentals, the property management, I'm maximizing as much AI as I can possibly for that. Yeah. And no one likes to go through mail. So that's a really good idea. Paper clutter. And then moving into property management, obviously, since you've been in the game for a while. You started before there was AI, of course. And then before there was a lot of technology available to really streamline property management.

I'm curious, what's like the biggest impact that you've noticed in your business? Well, I'm going to set the stage for you of what it was like when I first started as a property manager. So this is before I had my own. It was a small office inside of an apartment complex. There was no window, no AC, no heat. There was a small attached bathroom. And when I walked in that first day, there was a desk with a drawer full of keys, half of them not even labeled to what they are. And then a box full of one-page lease agreements. And then there was a piece of paper on the table that had gridline. on it made by a ruler and a red marker. It would have the tenant's name on one side and the month across the top, all the different months. And there was a checkmark if the tenant had paid their

rent or not. And this is for a 40-unit apartment complex. So taking it from day one of what I saw day one property management to now is like completely different. Yes. That's absolutely crazy. I can't imagine. I think my apartment complex is still doing it like that. That's awesome. And then do you want to do like a contrast of kind of what it looks like for you now using technology and AI? Yeah. So like even from that first day, I started building out systems and processes and I started using QuickBooks. And then I switched to, you know, finding out that there's actually property management software out there that does all of this.

So today I use TurboTenant and I'm using, first of all, my favorite thing that I always rave about is the lease auditor. So putting in the lease agreement and then having it tell me all my properties are in New York, so it goes through and tells me like, here's regulations in New York, here's things you should change, here's, you know, recommendations we have or things you can't have and need to take out. So all of my leases are pretty different because I have a lot of single family duplexes and every property needs its own tailored lease agreement. So every time something's up for renewal, I'm always running it through that to make. good work but I love that I use the lease auditors well it's a it's a great tool and then if you

were starting over today with access to AI and modern property management software what would you do differently on day one so if I had that so the first thing is the onboarding of doing it right correctly getting as much information about my tenants and about the property as possible into the property management software and then actually finding out what resources and tools I can utilize in the property management software. Totally. I'll give you an example. I signed up with Hospitable for my short-term rental software over the summer.

And about two months went by and they reached out to me to do an onboarding call. And during that onboarding call, I learned about 10 different things that I wasn't even utilizing or taking advantage of. So I would say the first thing would be getting as much information as possible doing an onboarding call with the software company and then actually implementing all the tools and things. And it may look like one little tiny thing, like late fees, for example, having them automatically sent to your tenant, automatically charged to their account, automatically, you know, sending out notices that like it seems like a little thing, but that just takes something off your plate. You don't even have to think about it.

I love that, being proactive about trainings. And there's a lot of like training videos, demos available online. right now that are completely free. I see like educational classes on AI too all the time. So I feel like that's really good advice to get prepared, especially someone who's getting into it. Do you think that AI could replace property managers? I think to a sense. I think there's a lot of legal and compliance issues that maybe I could see, especially state to state as far as what the regulations are and what you can and cannot say, but I think it can cover a lot of the team. I still think there needs to be a property manager for oversight, but I could see pretty much the other roles like a maintenance coordinator.

Basically with TurboTenant now, I have the coordinator, the AI taking in the maintenance request, asking follow-up questions, asking for photos, doing all of that for me, that if you hire a property management company, they often have people that are working that answer the phone, take the maintenance request, and entered in. And like, that's already one position eliminated. Yeah. And that's a lot of overhead, too. Going off of that, has AI helped you cut down on the amount of team members you're paying, like assistance? Yeah. So I actually had one full-time VA and then one as-needed VA. And the as-needed VA was the one that was actually pulling my mail and sorting it and putting it where it needed to go. So now that I'm building out something, I had already let her go knowing that I didn't need that anymore.

And then my full-time VA I had when I was also managing another 80 units, me and my partner had put all our properties together to manage together. And then so when we were doing that, we had one full-time VA. And she was kind of did communications. She did lease renewals. But really, that was it. She was just there if tenants needed her. So, you know, she worked 40 hours. She was available by phone.

But now even a lot of people are used to just messaging in apps and don't even need to make a phone call or want to. So I just now that I have my properties, I think I have about 40 units right now. With those properties, I just, I can take care of it through the messaging. Like I don't need someone full time for. answering the phone. Totally. Yeah. And a lot of people hate phone calls. You're so right about that. How do you feel about your tenants using AI? And do you notice that they are using AI within your operations? I don't notice at all that my tenants are at all. I did have somebody reach out to me today that found an application link. They emailed me because they, and they, I asked how they got

the application because it had been something that had been listed like six months or ago and I didn't have it listed anywhere anymore. And they actually said they used, I think it was ChatGPT to find an apartment listing. Interesting. And it found my old link and had sent it to them. So they were like falling up because it said, you know, it's available in 2025 if it actually was. But they, because I was like, how did you find this?

Yeah, that's crazy. They had used AI to search for apartments in that area and it pulled that up for them. Interesting. I heard recently from one of our product managers who's also also a landlord that her tenant had reached out for a PDF of the lease because they wanted to put it into chat chbt for review which is interesting that's how i use our um a i lease auditor on turbo tenant yeah but i thought that was really interesting and just like the conversation there around like are you comfortable if your tenants are like double checking your work using

a i are you comfortable if they're using AI to communicate with you it's definitely an interesting conversation. Yeah. Yeah. Where do you think we need to be careful about relying on AI and where do we think some of those like downsides are? Yeah. So I think definitely in the the messaging. So for my short term rentals, I have messaging an AI agent that's messaging. And I think it goes really great. But then other times it's like, oh no, you shouldn't have said that. But I think, Overall, it's a lot better than I expected, but I still think there are some hiccups. And with having long-term tenants in most states, there's these more regulations around what you can and cannot say than a short-term rental guest of what can and cannot be allowed.

So I would say that would be one thing as to like with tenants, sometimes you have to be very careful of how you phrase things or not even tenants, but applicants. So someone asking questions like, do you accept Section 8? Hopefully your AI says yes and doesn't say, no, we prefer because my lease agreement said you have to pay by cash, check, or through the TurboTenant app. So now my AI is going to respond that, oh, no, these are the only three ways to pay. We do not accept Section 8. So that obviously would get you into some trouble. But that would be the things that I would think of is them following your list.

lease agreement or what you have written down to a T. Totally. And not the over all like picture of fair housing laws and things like that. Yeah. Do you still have an attorney reviewing agreements for you, or do you use AI for that as well? So I do once a year. I'll send one of mine, which is everyone's pretty, like all the units are pretty standard template. And then it's just like, oh, is this one shared parking or things like that I change. But I still do once a year to my attorney. And, I mean, it hasn't changed that much over the years. But the TurboTenant AI one, I really like for building it more specific to that property type. Yeah, I'm sure in the in-between as well, too.

Yeah. What do you think AI can't do yet that you wish it could do to make your life easier? I wish that my tenants could put in the maintenance request. AI could contact the vendor, have the vendor schedule, have the vendor update with the AI, to update the maintenance request for me to show that they've received it, that it's updated, and then have the AI agent follow up with a contractor after it was scheduled to make sure it was done. What was done, AI, put it into the notes of the work order and close out the work order. I feel like that's possible.

Okay, let's do it. Maybe future turbotinent feature, not promising. But that's a great suggestion. That would really change the game. is and I don't even do it. Daryl does it for me, but I, that's like really our only, besides actually going to the property and doing maintenance, that is like our only kind of interaction. It's like, oh, we have a maintenance request. And usually we just email it to like the vendors we work with a lot. We just forward the email to them and send it right from TurboTenet. But there's sometimes,

you know, we have to actually like find a contractor call and set it up. Totally. What do you see in differences from you obviously have a diverse portfolio from like midterm, short term, long term, and then also commercial as well. What do you see are like the differences and how you use it for each niche? I would say I'm pretty, I'm using probably more AI with short term rentals. Okay. Just because I think it's, I'm more active in the day to day of that than my long term rentals. Yeah. Where, you know, every time of, you know, I have so many guests per week that come into the properties, but I'm using AI to update my listing, using AI to tell me which photos to change the listing, just to like revamp it every once in a while. I'm having AI scrub

through my communication. What are like the three things that I should change to get better reviews? So I'm probably short-term rentals probably the most. I do have some commercial properties that I just have them in TurboTenant with my long-term ones. So those are pretty much. all grouped together. Awesome. Cool. And then what specific software, obviously, there's a lot right now are you using? And what would be your recommendation for someone who's not using AI at all right now? Yeah. So I'm using Claude right now a lot. I'm not really, I'm still using Chatsubit once in a while for like a Google search basically, but to actually build stuff out and doing Claude. So like another thing that I've built out in there is just I've updated like our rehab,

scope of work and our template for, you know, estimating rehabs, things like that. So I actually have it like pull data from our market as to, you know, looking at going and scrubbing information off of like the MLS as to like what kind of, you know, finishes do properties have and stuff. And then find me a price as to what would it cost to put in granite countertops like this. What are vendor contractors charging in the area and I do a lot of like deep research I guess for building my scope of work and estimating rehab too awesome I love that the number one the tool that I'm using right now and then for social content I haven't played around with this yet but I think it's um is it manis manus M-A-N-U-S so it's actually was bought by meta so it's actually integrated into

Facebook so you're trying to build social content and has access to a lot of data from meta to actually help you develop better social content too. That's cool. I haven't heard of that one. Yeah. And then another one for social content is Stanley. Yeah. So it's part of Stan for creators.

And Stanley goes in and it does like a whole review of your social media account. It analyzes what's working, what's not working. And then it gives you recommendations. Can build out a content calendar for you. A lot of things like that. Love that. And then going back to just getting started at the beginning of your journey, do you think that getting started without these tools has made you a better investor operator? Do you think that it's

shaped how you're operating today? That's a great question. And for short-term rentals, I was doing everything, including the cleaning starting out. And I think that definitely made me a better investor, being the person actually messaging on Airbnb, having to manually change the pricing, not knowing anything about dynamic pricing or I don't even know if there was back then but um for that definitely but for long-term rentals I think I could be just as far as I am now without having all the hands-on experience I think that there's a lot of um education like I think bigger pockets does a good a good job of this and I think turbotenant also as to as you're in the actual software there's little like you put your cursor over something and it gives you more information and just tells you

what's happening or what this does that like gives you an explanation. So I think with like long term rentals it would have made my life a lot easier. Final thoughts. Obviously I think we've talked a lot about how AI is super positive and there's a lot of great ways to implement it within your business and also your day-to-day life as well, which you talked about a little bit. Do you have any final thoughts on how AI is a game changer for landlords and should they be getting started right now or even yesterday? Yeah, I think for any entrepreneur or business, there are ways that AI can take off daily tasks off your plates. Yeah. You know, I used it a lot for like a deeper research at first and trying to, you know, understand something more or build something.

but now that it's gotten to the point where it can actually like take over your computer and move things and declutter things and build you things. I think every entrepreneur should be using it in their business. And I also think they should be training their employees to also take advantage of it. I mean, one of the things I used to not like it all whenever I would do speaking engagements and I had to do a presentation, building out that PowerPoint. I would dread it. And it never looked good. Like I'm not a designer anything. Tonight I'm doing a presentation and I put it into Claude on the plane ride here and within 10 minutes the thing was built.

I just put in what I wanted it to talk about and that was it. And it just built me this beautiful slide deck in the 20 minutes on the plane ride just with the information that I had given it. I love that. Yeah. I think there's so many time savers for yourself. for your employees. Yeah, design is a huge aspect of using AI as well. That's so funny you said that because I was literally going to ask you about your presentation tonight and if you used AI at all. But I love that because I wanted to tie it to our event tonight, but very excited to talk

to everyone in Denver and to have you here and thank you so much for this awesome conversation. Information in the description about connecting with Ashley and finding more of her amazing advice. but thank you so much for watching. Turbotenant is the all-in-one platform for landlords to manage their rental properties. From vacancy to tenancy, we have you covered with industry-leading tools and expert advice. Landlord better from anywhere for free at turbotenant.com.