Only speculate with money you can afford to lose.
+1. I'm averse to speculative plays in general and probably wouldn't do one here.
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I just got some initial feedback - listing agent says $16-18K after 30% onsite management fees (includes ads, booking, cleaning, etc). Association fees are $3300 and include insurance (may still need additional coverage of my own) and all utilities. Last year's prop tax was under $1K. Maintenance should be fairly low on 338SF of cinder block and generic fixtures, but then again, any building issues could be passed on to owners via special assessments or fee increases. If I assume another $3K/yr we're down to $8-10K (plus free use, sticking to shoulder seasons to avoid blocking out high-rent days).
This is looking like a potential winner with the right financing.
The background I've pieced together so far: built in 1999, condo development failed, bought out by a local investor and operated as a hotel, legally remained condos and have been resold variously to other investors and individuals. There are several listed at $99K with an agent who tried to steer me into the $200-400K range despite lower cap rates (classic upselling, not going there), one at $89K with reserved parking, and one at $86K with no parking. There's also apparently more inventory unlisted, to avoid flooding the market. Most of the present batch were offered at $139K this spring and dropped to $99K in midsummer, but I don't know if any sold. The $89K unit, probably my first pick, has been online ~120 days and may be on its second listing at this price. Internally, they're supposedly all about the same - decent condition, furnished, in operation now.
The slack market tells me they're still overpriced, and I may try testing the seller's motivation when I'm ready. So far so good.