If You Were Buying Your First STR Today, Would You Still Do It?

Question

I've been thinking about how much the short-term rental industry has changed over the past few years.

Between higher operating expenses, financing costs, increased competition, and changing guest expectations, investing in an STR today requires a different approach than it did just a few years ago.

As an STR owner and real estate professional specializing in investment properties in the Smoky Mountains, I've seen firsthand how important it is to understand the numbers before you buy.

But I'm interested in hearing from investors across the country.

For experienced STR owners: Knowing what you know today, would you buy your first STR again? What would you do differently?

For those considering their first STR: What's holding you back? Is it financing, finding the right market, managing from out of state, or uncertainty about profitability?

And here's another question: Are you still actively looking to acquire additional STR properties in 2026, or are you sitting on the sidelines?

I'd love to hear different perspectives from both experienced and aspiring investors. Let's have a real conversation about where STR investing is headed.

Jorge Vazquez · Answer

I own 2 STRs and about 38 long-term rentals, and I still prefer long-term rentals. If I were buying another STR today, I would focus more on corporate rentals and 30+ day stays, targeting traveling nurses, insurance companies, relocating families, and business professionals. I've found this strategy works better for me than relying on vacation rentals, especially in suburban markets. Fewer turnovers, more stability, and less headaches. I would also make sure the property works as a regular long-term rental in case the STR strategy doesn't work out. I'm not against STRs, but I think having multiple rental strategies is the way to go in today's market.

Michael Baum · Answer

I would. If the deal made sense in an area that had strong owner support and near zero risk of restrictions.

Having said that, there is no way we could afford our lake house if we bought it now let alone cash flow like we are.

Matthew Tregoning · Answer

From the management side, I’d spend more time on the ordinary Tuesday before getting excited about the peak weekend. Who handles a failed lock, a missed clean or a leak when you can’t get there? Before adding a second place, I’d want the first to run for a week without me personally solving every problem.

Karen Cubberley · Answer

That makes sense—having places you enjoy was part of the return for you, too. And your point about buying the second one before getting through the learning curve is helpful for someone just starting out.

What would you want to have figured out with the first property before buying another?

Mike Grudzien · Answer

Michael hit it: the deal has to make sense. It's all in the numbers.

John Racine · Answer

Karen, yes, I'd still do it. I'd just go in with a different plan than most first-time STR buyers.

I started in long-term rentals in Orlando, and I still underwrite like a landlord. Before I look at nightly projections, I want to know what the place rents for as a regular long-term rental. If that number doesn't at least cover the costs, I walk away, and I leave tax benefits out of the math. Nightly revenue is the upside, not the reason the deal works.

The bigger change is how I fill the calendar. Most of my units now run as a mid-term/short-term hybrid. Monthly-plus stays are the base, and short stays only fill the gaps in between. Fewer turnovers, steadier income, and if nightly demand dips or local rules tighten, the property doesn't need a new plan. Some of my best stays started as a one-month booking that kept extending.

As for 2026, I'm still looking to buy. I want to use private lending rather than a lot of my own capital. In the meantime I've been growing on the co-hosting side, managing STRs for other owners (disclosure: that's my business). It's been a much cheaper way to scale than buying or arbitrage.

Andrew Steffens · Answer

I am a property owner, STR property management company owner, and broker specializing in sales in the Tampa area and yes, I would do it again. Especially now. When I was first getting into it a decade ago the tax benefits were not as robust. I am still buying today, with 2 purchases this year and will be getting another soon. Would I do things different? Sure. Mostly things in hindsight, like picking better properties early on. However, those still worked out with equity. That is like saying would I buy Nvidia 10 years ago!

Shalom Kaiser · Answer

Yes. Different buy though. 12 years doing this in Colorado, 30+ launches, still own 18, and the lesson that stuck is the rules matter more than the house. Pretty cabin in a town that rewrites its licensing next year? Bad deal. Now I want the license to be the boring part, and I want the numbers to hold up even if it ends up a mid term rental. Still buying. Just pickier. Looking at Colorado? Message me.

Jimmy Lieu · Answer

Thanks for starting this, Karen. Short answer for me is yes, I'd buy again, but I'd underwrite it more conservatively than most people did a few years ago. Well-run short-term rentals generally land around 15-20% cash-on-cash and tend to bring in roughly three times what the same house would as a long-term rental, but that only holds if the deal works with realistic occupancy, higher cleaning and utility costs, and a furnishing budget you've actually priced out.

What I'd do differently as a first-timer is run every deal through a plan B before closing. If the property still pencils as a mid-term or long-term rental, a soft season or a regulation change is an inconvenience instead of a crisis. I'd also hold a real reserve and check local permit rules before making an offer, since those can change the whole math.

On our side we run short-term rentals here in Columbus, and it's been a really strong fit for us. Happy to connect and compare notes.

Jules Aton · Answer

If I got the same deals or better than when I purchased yes. Mine were more about rebalancing my portfolio and having vacation places than income producing RE investment. What I wouldn't do is buy a second one within 11 months because there was a much bigger learning curve as compared to what I remember decades ago when I started with LTRs. Overall they were decent deals, have appreciated and we really enjoy them.

If You Were Buying Your First STR Today, Would You Still Do It?

If You Were Buying Your First STR Today, Would You Still Do It?

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