My Check-In Podcast co-host Sarah Nan DuPre tells a story that perfectly captures what actually matters in property management.
She rented an apartment in southern Spain over Christmas. Asked twice before checking in: “Just making sure there’s an oven. Please confirm.” Confirmed. Yes, there was an oven.
Before they checked in, she went to the grocery store and bought a Wellington roast, pork ribs, things that need an oven for Christmas dinner. They arrived at the apartment to find a microwave. Not a microwave with oven functionality. Just a microwave.
She messaged again: “Are you sure this is an oven? This looks like a microwave and we have all these things to cook.”
The owner called her personally on December 24th.
“I know you’re going to have to cook your Christmas dinner, and I just feel awful,” he said. “I don’t know who told you that we had an oven, but there’s no oven in that unit. Listen, I’ve got options for you.”
Option one: “I live about four blocks away, so you’re welcome to come over and use my oven. It’s your Christmas meal.”
Option two: “You can let me know and my wife will come pick up the meat. She’s a really good cook and we’ll cook it for you and bring it back.”
Sarah ended up asking ChatGPT what to do without an oven. It suggested a pressure cooker. She called the owner back: “Any chance you’ve got a pressure cooker?”
He did. He brought it over personally. Along with polvorones, traditional Spanish Christmas sweets. Not the cheap ones. The nice kind.
That’s what makes the difference. Someone calling you on Christmas Eve, offering you their home oven, bringing treats along with the pressure cooker.
Compare that to Sarah’s other check-in experience on the same trip. She messaged two days before: “I have to work in the morning. Where can I work from? Can we check in early? Where do we leave our bags?”
No response. They spent four hours on the street with all their bags while she tried to find a cafe.
The second apartment was nicer. Better furnishings, better location. But it got a far worse review because of the human element.
This is what the conversation about AI and property management misses. The technology doesn’t replace the job. It liberates you to do more of what actually creates value.
The Mistake That Reveals Everything
That whole Christmas Eve situation started with a mistake somewhere in the system. Someone tagged the wrong information. Data got pulled incorrectly. A microwave got listed as an oven.
Even with a fully automated AI process, mistakes will occur because there’s human input somewhere. Maybe the data was pulled from an OTA where the wrong tag sat with the wrong piece of information. Maybe someone clicked the wrong box when setting up the listing.
It’s not a perfect world. Far from it when it comes to how different software systems speak to each other at the moment. Translate that into an AI world with a fully automated system and no human running it or being accountable for it, and the minute something goes wrong, you’re in trouble.
Which is why AI isn’t here to replace property managers. It’s here to free you up to be the person who goes: “Right, I’m going to rectify this mistake. I do have the time to go get you a pressure cooker and turn up at the house.”
If you’re lifting your head above the water because AI is handling the routine tasks, that’s the time to double down and put your time back into the hospitality.
What Makes a Holiday Memorable
I went for a run this morning with our friend Ben Painter, who’s featured on a previous podcast episode (The Asset-Light Advantage: Why Kasa is Scaling While Others Are Crashing). We were talking about what makes a holiday memorable.
It’s not the thread count of the sheets or whether you have a smart lock. It’s where you feel like you’ve been welcomed by someone who knows the area.
Don’t make that mistake. Go to this restaurant. When you go to this restaurant, they know me really well and they’re going to give you the best seat. It’s all about the personal touch. That’s what makes the holiday memorable.
Sarah experienced this too on her Spain trip. As soon as she checked in, the owner sent a list on WhatsApp: “If you’re looking for a really nice cut of meat, this is where you should go. If you’re looking for fried fish, here. For tapas, here.”
His personal top 10 spots for everything in the city. Easy to navigate on WhatsApp, keeps you out of tourist traps. They found some really nice places through that.
This is hyper-local knowledge. It’s going back to the core of what we talked about when we first started this podcast years ago. Understanding what you’re offering, building brand identity. Your niche might be skiing, or it might just be your city that you know better than anybody else.
The best property managers I speak to are constantly thinking about the long-term health of the properties they manage. They’re recommending preventative steps. Maybe it’s time for a repaint. Maybe it’s time to do some damp-proof coursing in this room. The roof might need looking at.
They’re moving beyond the A to B of “booking scheduled, clean done, next booking” to threading the whole experience together.
This should be front and center on your website. Not just “Look at all these channels we can put you on” because anyone can do that. It’s “If something goes wrong at 4 in the morning, we’ll be able to fix it because we have the infrastructure in place.”
Your Cleaners Are Your Eyes and Ears
I often hear it said that your cleaning team are the most important people in your business because they’re your eyes and your ears.
AI can easily dispatch a cleaner. Schedule them, reschedule if they cancel, find a replacement. That’s what the technology does.
But having those eyes and ears helps you spot long-term problems. Damp, mold, construction across the street that looks like it’s going to take years to complete.
The best property managers are thinking beyond just task completion to the actual condition of the property. They’re looking out for things that affect bookings six months from now, not just next week.
Sarah shared a brilliant example. The architect she worked with when she purchased her rental property in Barcelona used to specialize in Airbnb properties before short-term rentals became heavily regulated there.
When she’d complete construction, the owner, the architect, and a couple of contractors would all host a dinner party in the property. Not just to celebrate, but to figure out what it’s like to actually cook a meal there. What are we missing? What haven’t we done properly?
You sleep there to test the water pressure, test the hot water, all the things you wouldn’t think about if it’s just a rental unit. They do it once a year as well.
You can absolutely tell as a guest when someone has cooked a meal in that property and when they haven’t. You notice the missing spatula, the lack of a wine opener. Things like that where you think nobody has actually used this kitchen.
That makes a huge difference. For many people, that’s the reason they choose a short-term rental instead of a hotel. The ability to feel a bit more at home.
A lot of wear and tear detection comes down to the cleaners. It’s easy to view cleaning as part of the process you need to optimize for cost. But this is where you shouldn’t be cutting corners.
It’s worth paying an extra few pounds an hour to a cleaner who does a really good job and informs you: “There’s a smell here. This is happening.” They might even coordinate with someone to come fix it or be there to let maintenance in.
This is about trust. You need a really good relationship with your cleaning team so they’re bought into your business. They go the extra mile.
Some people use outsourcing alongside their own staff, especially for peak seasons. But having that core team you trust might cost a bit more, but it saves you money in retaining owner relationships and taking a preventative approach to maintenance.
Spending a penny upfront to save a pound at the back.
The Local Network Advantage
That same principle extends to your handyman, your plumber, your electrician.
The smartest property managers I speak to either they’re very good at doing that sort of thing themselves, or they have a person for everything. They know how much money they spend every year with each person. They’re building professional relationships.
If you manage 50 units in a city, work out how much business you’ve thrown to the plumber, the builder, the electrician. It’s likely to be half a million dollars by the time you’ve gone through a couple of years of partnership.
That shouldn’t be a one-and-done “schedule a handyman, move on” approach. It should be about building a relationship so you’re the first call they answer.
When they see your number come up: “Oh great, it’s Leo from ABC Villas. This is an important client.”
That idea of networking locally is super important. You’re in your community, hyper-local. You’ve got a guy for plumbing, a team for cleaning, an electrician you trust.
This saves you money and enhances relationships with owners. It’s how most successful property managers work today.
Showcase that. It needs to be front and center in your owner pitch deck. Not “Look at all these channels we can put you on” because anyone can do that.
It’s “If something goes wrong at 4 in the morning, we’ll be able to fix it because we have the infrastructure in place to do that.”
Being professional. Being accountable. These are skills people in our industry have been demonstrating the whole time with their businesses.
The hope is that AI liberates them from the day-to-day so they can focus on doing more of that and use the additional time for surprise and delight elements.
Being a local actor is very important. It’s the way to grow.
What Owners Actually Pay For
There’s going to be continuous growth in people choosing to go it alone with an AI-powered software stack. Depending on how technical they are, they’ll buy something off the shelf or thread their own system together.
In some respects, that’s always existed. Individual hosts are still the mainstay of the industry. Most properties listed on Airbnb are managed by individual hosts.
What’s interesting for the property management and co-hosting community is how you convince the person who’s tempted by the 2% software option versus your 15-20% management fee.
Some people will choose the self-service path. That’s fine. Accept it.
Your job is to articulate value for the person who’s wavering. Even if it is 15-20%, they’re still making 80%. What are you doing to make it worthwhile?
For me, the big thing is out-of-hours hassle. Four in the morning lockouts. Not wanting to engage with guests personally. The unexpected problems.
It’s impossible to reasonably predict you’ll never have to engage with guests if you’re just using software and technology. Someone will need a pressure cooker on Christmas Eve. Someone will lock themselves out at 3am. Something will go wrong that requires judgment, not just task completion.
I don’t think the 15-20% management fee is a thing of the past. We’re just entering a world where people who want to do it themselves have better tools.
Focus on the people wavering between the two options. Show them what they’re actually paying for.
The Community Advantage
Local councils want to speak to a human being. They want to know they can call up Rachel who manages three properties in their neighborhood rather than calling some generic company and trying to reach the right person.
Neighbors can be really valuable. They can tell you when there’s a party happening, when something seems off, when there’s potential damage occurring. They can be your eyes and ears as long as they’re allies.
Managing those local relationships means it’s not just your cleaners coming in and seeing the property. It’s also: how do I better select the guests? How do I make sure this property is part of the community and not some antagonistic element?
A lot of that requires having a human being rather than chatting with a chatbot.
We’re going to see more property managers getting particular about what they take on. I’m hearing this more and more. “I have 50 properties now, but I’d rather have 30 of the right kind.”
What are the right kind? Larger properties. Four-plus bedrooms with lake views or something distinctive. Really special traditional vacation rentals.
The logic is sound: “I have the same amount of work for a four-bedroom house on the lake that earns me three times what this two-bedroom in the city earns. I’m going to focus my portfolio there.”
When someone comes with a different type of property, they don’t take it on. It’s not worth the hassle.
This creates an interesting dynamic. The industry is getting more competitive, but in an unexpected way. There will be owners who want someone to manage their property, but nobody wants to take it on depending on what kind of property it is.
Property managers want to streamline. If they can make the same money with 15 properties instead of 50, why wouldn’t they?
They get fewer inquiries on larger properties. Different caliber of guest. Less wear and tear. Guests tend to be more satisfied because they’ve planned farther in advance. They’ve researched the property in more detail than someone who booked two weeks ago and is now causing problems.
That property manager is carving out a niche. Specializing in larger properties because they know who the guest is. The more they know their guest, the more they can find them.
In the case of larger, more expensive villas, guests are less likely to book on an OTA anyway. They’re looking for something very specific. They want a conversation. Their PA wants to make sure the property is safe, secure, private.
When people find their groove, they understand they’re not looking to be mass market. They’re looking to specialize. That allows them to provide better service.
It’s very typical when you’re starting out to be obsessed by how many properties you’ve got. When you’ve been in it a few years, you’re more likely obsessed with how much revenue you’re making.
People set off in growth mode. Get the metrics up. Then they come back to: “We’re generating £10 million a year. That’s a really good place for us to be. It supports our staff and allows us to provide a really good hospitality experience.”
What This Means Going Forward
AI should liberate property managers from tasks so they can focus on what creates value: local knowledge, judgment, relationships, accountability.
The human element is what matters. Breaking down barriers with guests. Calling when they check in: “Just making sure you got in okay. Anything we can help you with? Do you need more towels?”
That alone is more powerful than an automated message. Everyone knows automated messages are automated. But the second you break that barrier, they’re thinking: “My host just called me. They didn’t want anything from me. They just wanted to know how my check-in was.”
That sets the tone for the rest of the trip. They know they can reach out. They know there’s a real person there.
The technology gets better. The software improves. The AI handles more tasks. That’s not a threat. That’s an opportunity to double down on what made you good at this in the first place.
Someone still needs to show up with a pressure cooker on Christmas Eve. Someone still needs to know the best restaurant in town and call ahead to get you a table. Someone still needs to notice the damp forming in the corner and sort it before it becomes a bigger problem.
That’s what you can’t automate. That’s what owners pay for. That’s your moat.
Want to hear the full conversation?
This article is based on an episode of The Check-In podcast, where Leo Walton and Sarah Nan DuPre discuss the future of short-term rentals.
Listen on YouTube, Spotify, or Apple Podcasts.
