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.

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!

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

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