Ashley:
What if the software that every rookie landlord on Facebook keeps telling you to use is quietly the wrong one for your first rental?
Tony:
Or maybe you’ve been saving for a year to buy your first short-term rental and then your city passes an ordinance that kills half of your night’s overnight. Is this short-term rental even worth it in 2026?
Ashley:
And for anyone watching right now thinking there’s no way in without capital, what if wholesaling actually might be the doorway, but only if you do it the right way on day one? We’re answering all three today on Rookie Reply. This is The Real Estate Rookie Podcast. I’m Ashley Kehr.
Tony:
And I’m Tony J. Robinson. With that, let’s get into our first question for the day. So question one, which comes from the BiggerPockets form says, “I’m curious what you all use as property management software to screen tenants, create applications for tenants to apply, create leases, list of properties for rent, maintenance, et cetera, et cetera. A do- it-yourself program that is landlord friendly to a beginner landlord. Right now I’m using Avail and I’m not loving it as I cannot upload my own rental application. What do you all use for your properties? So Ash, our resident long-term rental property manager, Queen. You’ve used a lot of different softwares, right? So maybe just first just give us all the different ones you’ve used and then tell us what you’re using today and why.
Ashley:
Yeah. So I’ve used Rent-Ready. I’ve used BillDiem. I’ve used AppFolio and I’ve used TurboTenant. So I have not used a Val that was talked about in the question, so I really can’t give any kind of opinion or preference on that. But I will say there are categories of how many units you have as to which long-term rental property management software you should select. So when I was using AppFolio and Buildium, I had at least 40 units plus. They have a minimum fe that you have to pay no matter how many units you have. So if you have one unit, you don’t want to pay AppFolio’s $200 minimum, they’re going to charge you every single month because that could be all of your cash flow. So there are these superior property management software that just has more bells and whistles. Ultimately, most of them do the same thing.
They have tenant screening, they collect rent online, they have messaging capabilities. So some of the ones, if you have 50 units or less, rent ready, turbo tenant, I’m pretty sure a Val is kind of in that category of property management software as to you don’t have a ton of units. What I would look at is do demos and look at the user interface because I do think that is really important as to how you interact with the software if you’re actually going to enjoy using it. Because if you don’t like logging into it and you get frustrated and you can’t figure things out and you don’t like the way it’s viewed and the dashboard looks, you’re not even going to implement it or use all the things it has to offer anyways. So do a demo on each of the different softwares that you’re interested in looking at.
And the next thing is compare their capabilities. So TurboTenant, for example, that’s what I use and they have a lease auditor. So you will upload your own lease agreement and you’ll tell them what state you are in and it will go through and do an audit of your lease agreement to make sure that it complies with all New York State laws and rules and regulations. It will also give you recommendations of maybe things you should add in there. So I don’t know of any other software that has that right now, maybe some of the bigger ones that I don’t look at anymore, but I really like that feature of TurboTenant. So I think also look what you want to get out of property management software. So is it the ease of the screening process? Is it just rent collection? And then also look at pricing too.
You don’t want to kill yourself on pricing if you only have a couple properties and you just need the basic features of the property management software too.
Tony:
Ash, one last question. How painful is it to switch from one PMS to the next? Let’s say that someone tries out one of these ones and they’re like, ” I don’t really know if I want to keep this one. I just want to jump to something else. “Having gone through that yourself, is it somewhat seamless to move or is it really like, man, there’s a lot of switching costs?
Ashley:
When I did it myself, yes, super, super painful. When I did it, this is probably five years ago, six years ago and moving it all over, you would have to download every document, every receipt, everything that you had in there, move it over to the new one. So one recommendation I do have is I do keep double records and yes, this is more work, but if you ever do switch software, even if you’re using QuickBooks or things like that, I still do this even for bookkeeping is I’m saving in Google Drive a receipt, the lease agreements, any documents for that property for that tenant, then I’m also uploading it so that I don’t have to go in and manually download everything. Right now, a lot of property management software has help with onboarding. So they will help you go through the onboarding process. This should be free.
Whatever one you’re looking at, if they try and charge you, maybe you should be looking at another software, but do an onboarding call for them to walk you through that process and how to do it. The second time I did it, I actually hired a virtual assistant at $8 an hour. I made a Loom video saying,” Here’s one tenant, here’s the information I want you to get from the property management software and here’s how I want you to put it into the new property management software. “And they went through and did it all for $8 an hour. I don’t remember how much it ended up costing me, but not a lot of money at all to be able to move data from one to the other.
Tony:
And honestly, you could use something like Claude today to probably automate that for you now.
Ashley:
Okay. So we have to take a short break, but you may think picking a property management software is the hard part, but maybe it’s you’re finally ready to buy your first short-term rental next month and your city just rolls out new short-term rental rules that basically are going to wipe out half of your projected income. So let’s talk about if short-term rental investing is even still a strategy that will work in 2026. We’re going to break that down right after a word from our show sponsors. Okay, welcome back. Our second question today says,” I’m a beginner investor looking to get started with short-term rentals, but I’ve been following the news and it seems like many cities are tightening regulations, issuing stricter permits and enforcing occupancy rules. I’m trying to understand whether short-term rentals are still a good strategy in 2026 given these changes. Any insights, personal experiences or advice would be greatly appreciated.
I want to make sure I start on the right foot without running into unexpected legal or financial issues. “So Tony, I took the first question, this one’s all you.
Tony:
So it’s a great question and I know a lot of people have questions about the regulatory landscape for short-term rentals, but here’s what I’ll say guys is that the presence of regulations in an industry is not the end of that industry. If you think about every other major industry that exists in the United States, there’s typically some level of regulation within that industry. I think what makes short-term rentals a little bit more jarring is the fact that there weren’t a ton of regulations because short-term rentals just weren’t all that popular. And as they exploded in popularity, we just saw so many cities reacting to try and keep up with the pace of short-term rentals in their cities and their counties. So the mere presence of regulations is not a bad thing. Now that said, I think that there’s two different ways that you can approach regulations as a short-term rental operator.
The first way is to choose cities that are economically dependent on short-term rentals. And then the second way is to choose cities where you have multiple exit strategies, and I’ll break down both of those. For the first way, choosing cities that are economically dependent on short-term rentals. Think about a comparison between a city like New York City and a city like Destin, Florida. New York City effectively banned short-term rentals a couple of summers ago and they did that because New York has zero economic incentive to protect short-term rentals and the revenue that they generate. When you think about New York City and you think about all of the different industries that exist, they have everything. They have multiple professional sports teams. They have Wall Street, they have business headquarters, they have literally every potential industry exists with some capacity inside of New York City. So for them, the little revenue that short-term rentals generates is like a drop in the bucket, maybe not even a drop in the bucket, right?
Whatever is smaller than a drop in the bucket. That’s how New York City viewed short-term rentals. So of course they had no issues in banning Airbnbs. Now, if you take a market like Destin Florida, it is almost the exact opposite of New York City. There are no business headquarters. There’s no major international airport. There are no universities. There are no major medical centers. There are no professional sports teams. There’s nothing there except for people coming in, spending a few nights at short-term rentals, spending money in the local economy, and then going back home. So for a market like Destin where travel and tourism is truly the backbone of that economy, they actually have a strong economic incentive to protect short-term rentals. So that’s the first approach is to find cities where maybe there’s a smaller permanent resident population, there’s low diversity of industries there and where travel and tourism is truly the backbone of that local economy.
That’s one way to reduce regulatory risk. The other way to reduce regulatory risk is to go into a city where you’ve got multiple exit strategies. There are some folks that work within our coaching program who’ve bought in Pittsburgh and Pittsburgh might not, at the surface level, seem like a place that’s a great location to go buy a short-term rental, but when you look at the data, it actually is pretty strong. However, Pittsburgh also has a really large permanent resident population. Pittsburgh has a lot of the things we talked about in New York City. So the regulatory risk in Pittsburgh is inherently higher than a place like Destin. So as we’re working with those folks, well, then the question becomes if we can’t short term in Pittsburgh say regulations change, can we midterm profitably? Can we switch to 30 day stays or more and still be profitable?
Could we, in a worst case scenario, long-term rent this thing and at least break even for us? So that’s kind of like the cascading way that we look at it is option one or option A would be high economic dependence on short-term rentals, or then option B would be, “Hey, let’s give multiple exit strategies.”
Ashley:
I think that goes with all strategies, to be honest. We’ve seen a lot of our friends have midterm rentals and have to pivot to long-term rentals because short-term rentals weren’t allowed in that market and the traveling nurses weren’t there anymore as much as they were and they actually had to go to long-term rentals or sell their property. So I think what you said is really important, being able to pivot and make sure the property has those exit strategies for any strategy that you buy it for. All
Tony:
Right guys, we’re going to take one quick break, but while we’re going, if you haven’t yet subscribed to the Real Estate Rookie YouTube channel, you can find us @realestaterookie and you can see mine and actually smiling faces. And last, if you want to be a guest on the Real Estate Rookie podcast, head over to biggerpockets.com/guest and get your application in. And we’d love to feature your story to inspire the next generation of rookie investors, but we’ll be right back after a quick word from our show sponsors. All right guys, welcome back. We are onto our final question and this question says, can anyone provide some advice on getting started with wholesaling and how to find good, reliable investors as well? Thank you in advance. All right. Wholesaling, what is it? We actually just interviewed Janelle Carlson. So if you look up Janelle Carlson, you’ll see an episode we did with her where she talked about finding off market deals and the bulk of her business is in wholesaling.
But for our rookie investors who are not familiar with what wholesaling is, wholesaling is basically the act of selling contracts in real estate. So you go out and you find a below market valu property, you then get that property under contract and then you sell the rights of that contract to an in buyer, typically another investor who’s going to flip it, bur it, whatever it may be. So that’s what wholesaling is in a nutshell. And the reason that wholesaling is I think attractive to a lot of newer investors is because you’re not actually buying the property. So you don’t have to come up with several hundred thousand dollars to buy the property. You are just getting the contract in place, which oftentimes costs nothing. And then you’re selling that contract at a profit. So it’s like arbitraging real estate contracts basically. So that’s what wholesaling is.
Now, how to get started, you can do direct mail, right? There’s a cost, you can put up billboards, you can run commercials, you can do a lot of pay-per-click. There’s a lot of different ways to get started. But for me, if I was maybe looking for ways to get started with very little capital, I think the easiest way … Actually, I’ll give you two easy ways because I’ve seen people execute both of these. The first way is to network with real estate agents. I have a friend who runs a wholesaling business based out of California and Nevada and the majority of his deals comes from him just cold calling, not homeowners, but agents and just telling these agents, “Hey, you’re probably going to find some deals that maybe aren’t a good fit for the MLS. Let me be your first call.” That’s all he says.
And he just all day, he’s just cold calling agents with that same spiel. And then every once in a while, one of them’s going to say, “Hey, I remember this guy who called. Let me give him a call.” And that strategy is somewhat smart because the agents are cold calling homeowners all day. So you can call one agent who they themselves are cold calling a lot of homeowners. So your reach expands in a way and kind of multiplies in a way that would be hard if you’re calling these homeowners yourself. And then I think the second way is just to partner with someone who’s already wholesaling in your market. But if you can just go partner with someone and say, “Hey, I’ll help source the deal,” whether that’s door knocking, whatever you want to do, but then you can partner with someone else who can show you the ropes of how to really scale that business up.
But if I were brand new, I had limited capital, those would be the first two things that I focus on.
Ashley:
Or look for somebody who’s wholesaling but wants to get into your market and you’d be the boots on the ground for them. So you put out in meetups or Facebook groups or whatever, get into the local wholesaling groups and put out there, I can be the boots on the ground. So even if it’s not a wholesaler that’s already doing it in your market, you could go to a wholesaler that already has a system, already has a process, has this business built and help them bring it into your market also too. The second piece of wholesaling is actually having, you can get the deal locked up, but having somebody to actually buy the property. So you need to build also a buyer’s list of once you get these properties under contract, you need to have somebody to sell them to. You could go ahead and list them on the MLS, but you also, if you can’t close on this property when the contract comes due, then you need to make sure you have a way out.
But most often the way to wholesale is to sell it to an end buyer. There are people that do go and what do they call it wholetaling where they actually do buy a property, do nothing to it and then list it on the MLS and sell it to whoever. But with wholesaling, you want to find buyers and that’s where going to the local meetups, not working with other investors in the area. I went to a meetup in Buffalo before where there was a guy, he was doing his first wholesale deal and he had a clipboard and he said, “This is the property I got.” H did his whole speech telling you all about it. And he’s like, “If you’re interested in this deal or any other deals I find in these areas, these are the areas I’m looking, put your name and your email.” Ends up, I knew exactly the house he had bought.
It was right around the corner from my parents’ house actually. And I think my parents live in a gray area, but this house was actually a meth house, came to a big surprise to my parents and someone raided this house near them. But yeah, it was a meth house and the people went to jail, whatever, and then I don’t know, it was foreclosed on something, whatever, and it got into this wholesaler hands, but he had no idea that it was actually a meth house.
So be very careful because you’d need to do some remediation with that. You just can’t and that property is sat and sat and sat and it finally sold. But just be careful and cautious of what you’re getting into if you do start wholesaling too, is all on that property he had to do was do a simple Google search of the address and all these news articles would come up saying that this was a house. But yeah, you want to find your buyers. And him going around that clip already, he had a ton of names on there just at the small local meetup.
Tony:
Ashley, just for my own knowledge, are you aware what does remediation look like for a meth house? What do they even do?
Ashley:
So that was my second Google after I confirmed that this was the meth house, that was my second one, but it’s like fire and restoration companies can do the same thing, but you go in because the meth can soak into the walls and the floor and everything. So I don’t remember exactly what it was. It was something that it’s recommended that it was handled by somebody licensed with chemicals and things like that to remove it out like you would asbestos or something like that, but it could eventually be a lawsuit if you find out someone rented you a house that was used as a meth lab.
Tony:
And you’re raising your kids in this house. Well, I learned something new every day in this podcast, so thank you for- That my
Ashley:
Parents lived near my house.
Tony:
That’s the one takeaway from this episode.
Ashley:
Well, thank you guys so much for listening to Real Estate Rookie. I’m Ashley, he’s Tony. And if you guys have questions, you can reach out in the BiggerPockets forums, put your question in there. Most likely it will be answered by another investor before we even get to it on the show, but we love your guys’ questions, so please keep them coming. We’ll see you guys next time.
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