$58k gross in a saturated market with real comps, or an emerging one where I'm guessing

File B has a cost problem you haven't priced. Two hours from a metro in a town of that size means your subs are whoever's available, your furniture delivery is a freight appointment, and a bad water heater on a Friday is a three-day outage because nobody's coming. On my last out-of-area project the labor line ran about 22% over the same scope in town, and that was with me driving out to babysit it.

The first professional operation angle is real, though. Forty listings and half of them tired means good photos and a made bed genuinely stand out. I'd just carry a bigger reserve in B than in A, and I'd want a name and a cell number for a plumber before I made the offer.

Harrow's right about the trades. In a town that size there's usually one guy who does everything and he's already busy. Get on his good side or don't buy.

You've described two different exercises and only one of them is underwriting. File A you can underwrite. File B you can only bound.

So bound it. What does the house gross at $150 ADR and 40% occupancy, which is a bad but survivable year in a thin market? What does it gross at 30%? At $268k the debt service is small enough that the answer might still clear, and that's the test. If B pencils at a pessimistic case, the tiny sample stops being the deciding problem, because you don't need the sample to be right.

File A is the one I'd push back on. 52% occupancy with supply up 38% year over year means your comp set is describing a market that no longer exists. Rerun A at 44% and low $180s ADR and see what happens to the $58k. If A only works at trailing numbers, you're buying the past. And on price, $520k for $58k gross before cleaning, management, furnishing, and platform fees is thin for a strategy this operationally heavy.

Quill, does file B have any midweek demand at all, or is it Friday and Saturday plus two holiday weeks? A market with one hotel and a state park sounds like a two-night-a-week market, and that caps occupancy no matter how good your listing is. The mountain market at least has some remote-work and long-weekend traffic mixed in.

I've got a place in a market that looked like your File A three years ago and it's now firmly saturated. What actually happened wasn't a collapse. ADR held better than I expected because the new listings were mostly bad, and my occupancy dropped about nine points while theirs dropped twenty. The compression lands unevenly. Well-run listings with 200 reviews keep eating and the new entrants starve.

That's an argument for A if you're genuinely going to run it well and stay in. It's an argument against A if you're going to be listing number 400 with zero reviews in June trying to build history in the worst possible season. Sextant's rerun at 44% is the right test either way.

The absence of an ordinance in B is a liability I'd price, not a neutral. Towns write rules after the listings arrive and the complaints start, and by definition you'd be helping the listings arrive. If you're one of forty, you're visible. Getting grandfathered depends entirely on how that state and town handle existing uses when they pass something, which is a question for a local land use attorney rather than a forum.

Also, ask what the state park expansion actually is. A funded, contracted, under-construction expansion is a demand event. A line item in a plan document is not. I've watched a market get bought up on the strength of a project that never broke ground.

Two document items before either of these.

One, in File A, if that's a condo or anything with an association, read the current declaration and the last two years of board minutes. Minutes are where you find out the rental restriction vote failed 11 to 9 last October and is coming back. The declaration tells you today's rule, the minutes tell you next year's.

Two, in File B, check the deed and the plat for private restrictions. Rural and river lots often carry old covenants about commercial use, and a nightly rental can get read as commercial depending on how that state's courts have treated similar language. No town ordinance doesn't mean no rules. It means the rules are in the chain of title and nobody's looked. Whether a specific covenant reaches your use is a question for an attorney in that state, but you want to know the language exists before you sign.

Fathom's covenant point is the kind of thing I'd have found in month five of my analysis and then used as a reason to keep analyzing.

Quill, the honest split here is that A costs $520k to learn a lesson and B costs $268k. I've stalled on bigger and better files than either of these, and the cheaper mistake is the one you survive. I voted B.

What does B do as a long-term rental or as a 30-plus day stay? That's the number I'd chase first. Two hours from a metro with a park nearby is at least plausible for monthly stays, and that's a floor under the thing while you find out whether the nightly demand is real. File A at $520k in a resort submarket probably has no floor at all, the long-term rent won't come close to carrying it. That asymmetry decides it for me more than the ADR comparison does.

$268k is high for a river town of that size, which makes me wonder what you're actually buying. In the low price point rural markets I track, forty active listings and one new hotel usually comes with houses at $140k to $190k. If B is priced at $268k, either the market already got discovered and the comps you can't see are already bidding it up, or you're looking at the nicest house in town and paying the premium for it.

Quill, what does the median sale in that town look like versus your $268k? If you're at 1.6x the median, the first professional operator advantage may already be priced in, and I'd go back to Sextant's pessimistic case with less room in it. Also worth knowing that roughly a dozen states don't make sale prices public, so if you're in one of those you're working from listing history and an assessor's opinion rather than actual sales.