What route to take for first time OOS investor

Question

Kerlous Tadres · Answer

@Mimi Lieder, if I were starting from scratch today, I'd skip Airbnb and go straight to mid-term rentals in Ohio, cities like Columbus, Dayton, or Cincinnati are packed with traveling nurses, remote workers, and corporate contractors who need 1 to 3 month stays, and that gives you Airbnb-level income without the volatility or the constant licensing headaches. Ohio's landlord-friendly laws, low entry prices, and strong rental demand make it one of the best remote investing markets right now, especially if you're chasing cash flow and tax benefits from day one.

Jimmy Lieu · Answer

Hi Mimi! Airbnb can still work in 2025–2026, but it’s definitely more competitive now and not as easy as it used to be, with results really depending on the specific market, local rules, and how well it’s managed. A lot of newer investors are finding that long-term or mid-term rentals are more stable and easier to scale, especially if they’re trying to build a portfolio remotely without constant operational headaches. If I were starting fresh today, I’d probably focus more on steady cash-flowing long-term rentals first, then layer in short-term rentals later once I understand systems and markets better. One market I’d look into is Columbus, Ohio—it’s been one of the stronger investor-friendly markets with solid population growth, job growth, and major companies like Intel, Amazon, Google, Honda, and others expanding there. You can still find properties that cash flow in the $120K–180K range hitting close to the 1% rule, plus strong long-term appreciation potential compared to a lot of overheated markets. Happy to connect and answer any questions you have!

Leah Walczak · Answer

The framing worth pushing back on: "Is Airbnb still a good play" is a sub-market-level question, but you're making a property-level decision. Both things can be true.. the category is more saturated AND a specific deal can still work, if you underwrite it correctly.I've been underwriting a lot of deals for Abilene as of late because of the data center boom.

The test I use: does the property cash-flow as a long-term rental at market LTR rent, with normal assumptions — 80% of market rent for safety, 10% vacancy, 20% opex? If yes, you get the STR upside on top of a self-sustaining LTR floor, and you can switch strategies when (not if) the local regulatory or demand environment shifts. If no, you're betting the entire deal on continued STR outperformance in a market that's statistically more crowded every year, with no escape hatch.

By that test, most 2026 Abilene STR deals I've seen don't clear the LTR-floor bar unless you're getting a below-market entry. AirDNA revenue looks healthy, but ADR has compressed and occupancy has softened, meanwhile, Abilene LTR rents haven't moved much. That gap is where deals get dangerous.

To your actual question: I'd start with LTR in a boring market where you can self-correct if something breaks. Get the first deal running smoothly and know your buy-box cold. THEN layer STR onto it, not the other way around. Starting with the highest-variance strategy in the hardest-to-manage remote market isn't impossible, but it's not the play I'd make for a first deal from NYC.

J Castro · Answer

Hey @Mimi Lieder, welcome to BP!This is a great question—and from a lender’s perspective, you’re approaching it the right way by comparing strategies instead of chasing hype.

Here’s how we’re seeing the market in 2025–2026:

1. STR (Airbnb) isn’t dead—but it’s no longer easy to finance or underwrite

Short-term rentals can still perform well, but the risk profile has changed:

• Strong, proven markets still show solid performance
• Oversupplied markets are seeing declining occupancy and      rate pressure
• Regulatory uncertainty is a real factor in many areas

From a lending standpoint, STR deals today are much more operator and market dependent, not passive or plug-and-play.

2. Market selection matters more than ever

We’re seeing deals struggle not because the strategy is wrong—but because:

• Projections are too aggressive
• Expenses are underestimated
• Demand assumptions don’t hold

Secondary and tertiary markets can absolutely work—but only when the fundamentals are there. As a lender, we’re focused on sustainable income, not optimistic projections.

3. How we view STR vs LTR vs MTR

From a risk and underwriting standpoint:

• STR:
     Higher income potential, but higher volatility and scrutiny
• LTR:
     Most stable, easiest to underwrite and finance
• MTR:
     Increasingly attractive—more predictable than STR, better upside than LTR

We’re seeing more investors—and lenders—lean toward stability with upside, rather than pure peak returns.

4. If you’re starting out (especially remotely)

From a financing perspective, the strongest borrowers typically:

• Start with a stable, cash-flowing asset (LTR or MTR)
• Build experience managing a property and understanding      real numbers
• Then scale into more operationally intensive strategies      like STR

The biggest risk we see is investors going straight into STR without systems, and the deal not performing as projected.

5. Final thought

You’re in the right place—platforms like this give you access to real operators who’ve already gone through the learning curve.

The deals that perform—and get financed most smoothly—are the ones built on:

Stable assumptions → proven demand → strong execution

Not just best-case projections.

If you want, I’m happy to walk through a specific deal or market and show you how it would be viewed from an underwriting standpoint so you can see what actually makes sense on paper and
in practice. Best of luck!

Mimi L. · Answer

Really appreciate this breakdown — this actually clears up a lot.

What you said about STR not being “plug-and-play” anymore is exactly where I’ve been getting stuck. It always looks great on paper, then the deeper I go it starts to feel way more operator-dependent than I expected.

The LTR/MTR angle makes a lot more sense to me, especially starting out and being remote. I’m mainly trying to build something stable that cash flows and grows over time, not chase best-case scenarios.

I’d definitely take you up on walking through a deal if you’re open to it — would be super helpful to see how you actually underwrite something vs. what I’ve been seeing online.

Min Zhang · Answer

Hey Mimi, most out-of-state buyers I’ve worked with actually start with turnkey long-term rentals. The main reason is stability and simplicity. With long-term rentals, you get more predictable cash flow, fewer operational headaches, and less dependency on things like seasonality, regulations, and day-to-day management. A lot of investors start with long-term rentals to build a solid foundation, then expand into short-term or mid-term rentals once they’re more comfortable and have a solid team in place. I always recommend seeking help for property manager for your out-of-state rentals. Hope this helps and best of luck on your investing journey!

Evan Hopple · Answer

@Mimi LiederLong-term rentals give you a more predictable base to build a portfolio on. STR works in the right markets, but it's harder to scale and more dependent on local regulation.

Alex Olson · Answer

To answer part of your question, Kansas City is a great market for out of state investors and mid term rentals work really well in all sub markets. Some sub markets have restrictions on STR.

Mimi L. · Answer

@Arman Ahmed Thanks so much for your time and for breaking that down! It’s a huge help to get that perspective on prioritizing stability over the STR hype, especially starting out from NYC.So, do you think I should focus on buying a long-term rental first? I’ve heard so many people say it’s not worth owning property if you aren’t there to manage it yourself. The common fear is that without being "boots on the ground," the overhead and lack of oversight just eat all your margins.In your experience, is the "passive" remote model actually realistic for a first-timer, or does the math only really work if you're local?

What route to take for first time OOS investor

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