Short-Term Rental (STR) Feasibility Checklist

Usually no — most cities across the Eastside and the metro core restrict in-city STR. That's why the feasible play for a local high earner is almost always a destination market (mountains, water, wine country) that allows it. Regulation is the first gate, before demand or numbers.

Because of the potential W-2 offset: if the average guest stay is seven days or less and you materially participate, STR losses can be non-passive and offset W-2 income. That's the mechanism a long-term rental generally can't provide — but it's fact-specific, so verify with your CPA.

That the jurisdiction allows STR — licensing, occupancy caps, and HOA rules included. A great-looking property in a market that bans or caps STR is a dead deal no matter how the numbers pencil.

Management (far higher than long-term, often 20%+), cleaning, furnishing, seasonality, and heavier upkeep from constant turnover. Model revenue as occupancy × ADR minus all of those — gross booking revenue is not your return.

Often, if the price and your tax situation justify it — cost seg plus bonus depreciation front-loads deductions that, with material participation, can offset income. Whether it pencils depends on your rate, so confirm with your CPA.

Pivot to a market that allows it and re-run regulation, demand, and tax structure there. Evaluating real STR-friendly markets is part of a Real Estate Review.