STR/Airbnb Q&A: AI Tools, Tasks & Revenue in 2026 (Part 1)

Welcome everyone. I'm glad you're here today. My name is Tim Hubbard. I'm the CEO of Coarsely, also the host of the Short-Term Rental Riches podcast, where a lot of you may have found us through. There's a lot of questions in the short-term rental space, and we talk with managers and owners and investors every single day. And we also manage over a couple hundred properties. And so we've got a lot of insights, and I'm looking forward just to having casual conversation around the questions that you've already submitted. So let's go ahead and jump into it. First off, yeah, I just want to welcome everyone. It's been a really long time since we had some group calls like this, and I'm excited to say we're going to be doing these more regularly. We actually have a couple of our own partners that have joined Coorsly on the call, but lots of questions just in regards to everything. And I guess, yeah, before we get started, for anyone that I haven't met before, my name is Tim Hubbard. I'm the CEO and co-founder of Coorsly. Coorsly, our name comes from this idea of being your core operating center on the back end of all your short-term rentals. So, you know, we're making the pricing decisions, we're handling the guests, we're handling task management. And excited to say we work with a lot of partners now in over 40 cities, which also gives us a lot of really good insight. So along with our partners' properties and my properties, we've got some real-world advice and excited to share that today. So why don't I just start off with this first one that has to do with pricing? And this came from Mark De Vita. Thanks for submitting this. It says, do you have any experience with Hospitable's dynamic pricing tool? I currently use PriceLabs. So for those of you who don't know, Hospitable is a PMS program. I actually, I think I interviewed their founder not too long ago on the podcast. Well, I can't say that I have personal experience with their tool, but I know every PMS essentially has a dynamic pricing tool. And why do they have it? Because dynamic pricing is an essential now. And a lot of the property management software companies have realized that their users are not using a dynamic pricing tool. So if you signed up for Hospitable, for example, Hospital can see if you're connected to PriceLabs, and if you're not, then they want to sell you the pricing tool. That's just how it works. They want to get more from all their current users. PriceLabs only does dynamic pricing. And so for me, a company that's focused specifically on one thing and doing that thing very well is usually always going to have a better outcome at that one thing. There's some challenges with dynamic pricing tools. I also had the founder of PriceLabs on the podcast, so you guys can go back and check that one out. But Some of the main challenges with revenue management that we've identified is, first of all, the data is not 100% accurate. So it's scraped data, meaning that they look at your Airbnb listing or Vrbo listing. Most of these platforms are only looking at that data. So the first thing is that the data is not 100%. Scraping means that they're looking at your calendar, they're seeing what your price is, they're scraping that data. And if your calendar becomes blocked, then they assume that you rented that night. But we all know, at least those that have been in the space, there are lots of reasons why we block our calendar. Maybe there was a maintenance issue. Maybe, you know, whatever it happens to be, you know, there's a list of reasons. Maybe we're using it personally for like 2 months. And so that data is skewed. And that's the same for PriceLabs. That's the same for Wheelhouse. That's the same for really any dynamic pricing tool, AirDNA. So what we like to do internally is we like to look at all the data we have access to. To make a decision. The more data we have, the more confident we can be with it. While we're on the pricing topic, a couple other things that we've noticed that are lacking in the dynamic pricing tools. For one, they don't account for your review scores. I know we got lots of questions today on reviews as well, and rightly so. They are one of the main points to driving your visibility for your property. And we know that more visibility with our property means more people are looking at it and more people are booking it, which means the property should be earning more money. And so to have a dynamic pricing strategy that does not incorporate that is a pretty big, pretty big miss. Excited that Corsi, we've got a tech team with us now. We're bridging a lot of these gaps. And so that's one of the things that we incorporate. Also a brand new property. You know, if you have a brand new property that just entered a market and it has no reviews and your competition has 55-star reviews, that's different, right? And so your pricing has to constantly be changing. So highly recommend using a pricing tool. And then I'll just leave you with one last flaw that we've found with revenue management and a lot of the current management practices is that it does a good job at adjusting your daily price, right? You know, just like an airline, if there's an event in town, if it's a weekend versus the weekday, if someone's booking 5 months out from now versus right now, it's adjusting all those prices, you know, based on market data and demand, but it's adjusting it based off a base price. That's what PriceLabs calls it, a base price. So you launch a property and you say, yeah, I think my property should earn $200 a night. That is the base price at which the dynamic tool is adjusting it every day, either up or down. But if your base price isn't right, then that means you're adjusting off like a faulty base, right? And so the way that we account for this is by looking at market data. And anyone using PriceLabs, anyone using AirDNA or the tools out there, you can get access to market data. If you are getting booked up much faster than your market, you're probably not priced high enough, right? And then the opposite is true. If the market's getting booked and you're not getting booked, then your prices are probably too high. And so we look at those things and we adjust that base price accordingly. Again, all based off, off-market data. That is really our benchmark, you know, for how a property is done. And if you're in a market where there's not a lot of data, then there's a lot of testing that goes on, right? But again, you have to be adjusting that base price to truly know if you're maximizing prices or not. Of course, if you have historical data, that's always a big help too. We've got some other pricing questions here. Here's one from Anne. Says, how far do you turn on your dynamic pricing? How far out do you turn it on? So our dynamic pricing is turned on for all of our available nights. We wouldn't want to have our property open for the next 12 months, for example, and only have dynamic pricing turned on for 10 months. So that's a pretty easy one. We want to make sure it's turned on all the time. This one's from Muhammad. I want to learn about revenue management. It is a bit of a study. It didn't used to be that way, but it should be that way. You know, in a hotel, it's the second highest paid position after the general manager, the person that runs the hotel, for example. But we know like in the airline industry, I mean, this is, this is where we see dynamic pricing going. We see it all being run by machines, right? I mean, you don't have someone at American Airlines that's like, I'm going to, I'm going to add a 5% discount on my Dallas to Charlotte flight today. It's all pulled off from data, right? And of course, that's, that's really, really complex. These dynamic pricing tools are allowing us to do a lot of these things easier. But at the end of the day, algorithms that can accurately predict all this based off information is where the, where the industry's headed. If you're not using dynamic pricing right now, it's a huge advantage to jump on those tools. If you do jump on it, there is a lot to learn. You know, these tools have a lot of it built in themselves, but make sure you're keeping account for some of the things that those tools don't currently incorporate. You know, there's really 3 parts to having an optimum property. We have to have a really good listing, one that stands out. We have to have really good pricing. If we have a really good listing and we have really good pricing, all the things we just talked about, but we don't have good guest management, then your property's not going to do well, unfortunately. So guest management is critical. I think a core component to starting with that is setting the right expectations, right? So we don't want to advertise something in our property that's, that's not there. If the backyard does not look great, people are still going to see the backyard when they check in your property. So we always encourage everyone to represent their property exactly as it is. Doesn't mean you need to put the backyard photos like your header photo, of course, but we want to make sure we have it in there. This question came from Beth Russell. She said she has one property. What, if any, PMS should I use? Well, that's a good question. With one property, the need for PMS is a lot less than, you know, even with two properties. I always highly recommend using technology because it helps us create better guest experiences, be more efficient. I worked my prior life, I worked for a software company in a different industry with automotive shops, and I sold business management software. Similar to what you, you would see in a PMS. The software I worked with helped manage the businesses, and what I found consistently, the ones that really embraced technology, they had better customer experiences. So in our case, guest experience, they made more money and they were less stressed out and everything was more efficient. So I highly recommend using a tool. There's several PMSs that can work really well for smaller amounts of properties. Hospitable is one that's kind of catered towards smaller portfolios. Hostaway and Gastee are probably two of the biggest ones in the industry right now. There are new ones popping up that promise a lot of AI technology, which we'll get to that in a second too. That's another common theme that came up. But the reality is none of them are perfect, right? Just coming back to the original question on using hospitals' dynamic pricing tool, they built that tool to accommodate a work better tool, basically. And so all of these PMS programs, are trying to do that with every, every feature. We internally used to use Guesty, great program. We currently use Hostaway, which we feel is one of the leading software programs. I mean, they're valued over $1 billion. They raised over $500 million. And so they've got a lot of resources to continue adapting their, their software. Any of those would be good. And the main things that those are helping with are channel management, right? To help you get on all these different OTA platforms, which is a really big piece of your performance with the property. So I would check out any of those. Here's one from Laura Lopez. Says, are you still using Notion as your database? Please share how it's used. So Laura, I would imagine, is probably a longtime podcast listener because I pretty much talked about everything I was doing in my personal portfolio. And this Notion episode came out a long time ago. The answer is no, we do not use Notion as our property database, although I do think Notion, for any of you that don't know, it's essentially a program that allows you to organize all your notes, all your data, your video, your links. Your files, everything that you can imagine, and in lots of visually pleasing ways. And they branched out to connect with all kinds of other software, but they're not designed specifically for short-term rentals. And because we manage a whole lot of short-term rentals, it's imperative that we have our information 100% accurate. And so we currently use a program called Conduit that houses— well, we're building our own internal database, I guess, is the long story short. We do have developers on our team now and The reason that we're building our own internal database is because we do use multiple programs in the industry, which we think that any serious operator has to be doing. It kind of goes back to that idea of using, using the best tools, but those tools don't all fully integrate all of the information with each other. So Hostway, for example, is a PMS that integrates with the OTAs or the online travel agencies like Airbnb or Booking.com, but it doesn't actually integrate 100% of the information. And then we're using this tool I mentioned is an AI tool that helps us with some guest messaging and it also stores required information for properties, but it's slightly different than what's in the property management software. So hopefully I'm not losing people here, but the idea here is that each of these tools has its own data that it needs and it's not all the same. So we're basically building our own central database. And you could do this with Notion still. I mean, if you're managing a smaller amount of properties, Notion has a lot of flexibility to track information. Properly. So nope, not using that anymore. We brought things in-house, but I still love that program. It's— I use it every single day. Jacobson, best reservation management system to handle guest communication. So this is something that's, that's changing. It's changing because AI has entered the space, right? And one of the things that AI is excelling at more so than any other industry is customer support. And I know a lot of us may have the idea of like really bad chatbots or entering, you know, customer support with like Comcast and getting an AI agent that asks the same question like 10 times. That's not the reality today. Reality today is that there are really, really good LLMs or language learning models that can answer questions a lot of times better than humans can, more consistently. You know, they don't forget things. They can access unlimited amounts of data. And so in terms of guest management with messages, it used to be a PMS. So, you know, Hostway or Hospital you would use to help you manage those messages. And that's still a really good tool, but most of those are not as developed with AI as tools built specifically for guest support. They have what you would call automations. They have ways to automate check-in instructions, for example, or they can automate a request for review. But we know that those automations don't fit every guest equally. Let's just say your check-in time is 3:00 PM and the guest doesn't arrive till midnight. Maybe they have a late flight or something like that. If you use a programmed automation, maybe it was set to send a follow-up at 8:00 PM to say, hey Josh, just want to make sure you checked into the property. Okay. But they already sent you a message that said they weren't showing up till midnight. Well, that doesn't look that great, right? And that's something that most PMS programs are still not able to accurately handle. Because they haven't involved all the AI yet. So with AI, it can read the messages and see, oh yeah, Josh said he's coming in at midnight, so it sends it at 12:30 AM. So there's just so much more flexibility with AI to the point where we don't use our PMS for messaging anymore. The internal tools in Hostway, we do not feel are nearly as, as good as the ones that we're using outside in a tool called Conduit. And so there are a lot of AI tools being developed specifically for the short-term rental industry. One of the big promises that you'll see is that they automate 95% of all your guest communication. You know, you can set up a property, you turn this thing on, it knows everything, it's set out perfectly. But we know that that's not the truth. There's lots of situations where we need humans involved to handle tougher decisions. Maybe there's information that a guest asked that you don't have stored in your database, so there's no way for it actually to answer. All of these Those things we handle on the backend through escalations. You know, we have, we spend hours and hours literally every single day adjusting this, testing this, and just the side of testing it is really challenging. So we test with my properties, which is nice. I know not everyone has test properties around, but we do that. We have quality control and we're just constantly, constantly messing with it. AI programs that promise that, yes, maybe they do a really good job at sending the basic information like, hey, what's the Wi-Fi password or what's the code to get into your property, but where they don't automate things is when you have complex workflows. So let's say this is an example that you want to allow early check-ins at your property. We know basically everyone asks for an early check-in, right? And basically everyone asks for a late checkout. I'm guilty. I do it as well, whether I'm at a hotel or short-term rental. But there's a lot that goes into that. First of all, we need to make sure the property is available. If it's available, has it been cleaned? Did we just have someone check out? How How far in advance does the guest actually want to check in? Maybe it's like 8 hours in advance where it's justified for us to charge them extra and the guests would be willing to pay extra. But then how much do we actually charge the guests? Do we charge them as a percentage of what the nightly rate would be, or do we charge them on like an hourly basis? So you can see how some of these workflows get really, really complex. And these are everyday things like literally everyone asks for a check-in and maybe your process isn't that complex, but for a lot of people it is, or, you know, for larger portfolios it is. So that's the part that is not being— that's not accurate when you're looking at AI tools in the market today. When they say that they're automating 95% or whatever it happens to be, they're considering just the basic guest messaging. So hopefully that gave you a little clarity. I think it's a super exciting space because it's improving the guest experience, you know, assuming we have all of our information accurate, right? And if you are building a portfolio, whereas we have multiple people responding throughout a guest stay, maybe it's a week-long stay. If you have someone helping you, you have multiple people helping you, there's different tones that maybe were going out. Maybe someone gets sick and so the messages was delayed a little bit. So there's all kinds of benefits from AI and it's getting better by the day. I mean, it is really, really impressive. Well, we received a ton of really good and important questions, questions that are undoubtedly on a lot of your minds that didn't actually ask them. As much as I would love to answer all of them in this episode, as you know, most of our episodes are quick and actionable. So we're going to go ahead and save some other important questions for for a part 2. Stay tuned as we jump into those next week.