Meet Jackie - Short Term Rental Owner - Q & A

What first sparked your interest in owning a short-term rental, and what made you decide to move forward with purchasing one?

We had been talking and dreaming about getting into short-term rentals for years. It was really about building some passive income and taking advantage of the tax benefits. It just felt like a smart move if we could make the numbers work.

What finally pushed us forward was connecting with the right people. Once we found someone who could guide us through the process and a tax professional who helped us understand how it would all pencil out, it went from “maybe someday” to something that actually felt doable. That clarity made it a lot easier to take the leap.

How did you approach finding the right property? Were there specific criteria you were looking for, like location, layout, or price point?

We saw a lot of houses. At the beginning, we thought we’d be really structured about it: price point, numbers, checklist. And those things mattered. We had a ceiling, and we knew it wasn’t just about the purchase price. We had to factor in repairs, maintenance, and furnishing the whole place.

But somewhere along the way, it shifted. After walking through so many homes, it became less about what checked the boxes and more about what we felt when we walked in. Did it stand out? Did it feel different from everything else we’d seen?

We kept coming back to how we travel. We love finding places that feel special, like “this is so cool, I wish this was in my own home.” So we started asking ourselves, would we actually be excited to stay here? Would our framily or friends love it? Would people remember it?

What was the buying process like? Was there anything that surprised you along the way, either about the market or the transaction itself?

Buying a house can feel a little unpredictable. The house we ended up buying actually went pending before we were ready to pull the trigger, and then it came back. We also loved the very first house we saw, but we weren’t ready to make an offer yet, and looking back, we probably should have been.  It was a good reminder that you really never know how things will play out.

How did you evaluate whether the property had strong Airbnb potential before making an offer?

We tried not to overcomplicate it, but we looked at it from a few different angles. Every time we walked into a place, we’d ask ourselves, does this stand out or does it feel like everything else?

We kept going back to how we travel. We’ve stayed in some really special places, and those are the ones you remember. So we’d picture ourselves as guests. Would we be excited to book this? 

At the same time, we had to stay grounded. We’d run the numbers and make sure it actually made sense with purchase price, furnishing, and ongoing costs. There were a few homes we liked, but once we really looked at it, they just didn’t work or maybe the work was more than we were ready to handle for our first property.  

Once you closed, what were the first steps you took to get the property ready for guests?

Once we closed, we jumped right into freshening everything up. It wasn’t a full gut remodel, but we wanted it to feel clean, updated, and really taken care of. We painted, refreshed the landscaping, steam cleaned, just bringing everything back to life.

From there, we focused on the little upgrades that make a big impact without going overboard. Updating fixtures, swapping out finishes, anything that felt simple but elevated the space.

How did you approach the design and furnishing process? Did you have a vision from the start, or did it evolve as you went?

Honestly my process was kind of WWJJD … what would Josh and Joe do. I’m definitely not a designer, but I love design, so I tried to trust my gut, have fun and pulled inspiration from the house.  The house kind of told us what it wanted to be. With the wood floors, beams, big front door, and especially the ironwork, we leaned into what was already there instead of trying to force something else.

A big part of it was collecting pieces along the way. Marketplace, consignment shops, treasure finds you can’t just go out and buy again. It felt more like curating the house than designing it.  We weren’t trying to create something you’ve seen a hundred times. It was more about creating a place you want to be. Somewhere you can hang with friends and family, move between all the little areas, and just enjoy it.

The speakeasy is probably the best example. It’s technically just a detached garage, but we turned it into our favorite space and it’s become a guest favorite too. When the iron doors open up to the courtyard, it just works. You get that perfect San Diego indoor outdoor vibe. You can go out and adventure all day, but you also have a really good place to come back to and just hang.

You chose to self-manage rather than hire a property manager. What does that actually look like day to day?

We decided to self-manage mostly because I have the time right now and we wanted to maximize the tax benefits.

Day to day, it can feel like a lot, especially in the beginning when you’re still figuring everything out. A big part of it is communication. You’re constantly trying to find that balance of what’s helpful vs too much, and every guest is a little different. You kind of learn that there’s no perfect formula.

Then setting up support services and solid scheduling systems is huge. That’s what keeps everything running smoothly behind the scenes.

What has been the biggest challenge so far, and what would you do differently?

Honestly, the biggest challenge has been all the random stuff you don’t even think about… like our thermostat. We were fully like “we’ll just upgrade it to a smart one,” easy… and then found out that’s not actually a thing for our system. Cool cool.  There were definitely a few moments of realizing we were very confident for people who did not totally know what we were doing.

If we were starting from scratch, we’d just expect more of that and roll with it instead of overthinking everything. You really do just figure it out as you go.

But it all worked out how it was supposed to. Trust the process, find the right house, and just make it work.

For someone on the fence, what’s one thing you wish you knew before starting?

Having the right people helps a lot. A good agent, a tax person, even a designer if you need one. It just makes things smoother.

And honestly, timelines. Give yourself more time than you think you need. It really depends on the house and how much work it needs, and it’s easy to underestimate that part. Give yourself some grace in the process, you’ll get it done and it will be awesome.