Some areas define it as anything under 30 days; others under 90.Midterm rentals often bypass short-term rental restrictions — but you still need:-Proper lease agreements-Local registration (in some cases)-Business insuranceIf you’re operating in gray areas, tighten up your paperwork.Anyone’s city recently updated their MTR regulations?

In a SF property, frankly, that creates a lot of gray areas. 

It’s very much a gray area—not expressly permitted under most zoning codes, yet rarely enforced unless a complaint is made.

Quote from @Andrew Gray: Hey BiggerPockets community,My name’s Andrew Gray, a former professional athlete turned real estate investor and mortgage agent.

That spread is what makes the model so compelling.It’s worth noting that zoning can be a gray area in some parts of metro Atlanta (Clayton, Fulton/City of Atlanta, Cobb, Gwinnett, DeKalb, etc.), but enforcement is limited and most operators stay well under the radar by keeping the property well-run and community-minded.If you’re considering one, my advice is to start small, learn the rhythm, and dial in your systems — cleaning, communication, and tenant screening are everything.

In other words, their coordination work during a sale falls under that part of the contract, not their normal management duties.Now here’s where it gets dicey — if you (as the buyer’s or listing agent) are stepping in to sell the property while the PM has an active contract that includes sales coordination rights, you could be stepping into an ethics gray area.

Publishing criteria (like “3x rent income” or “650+ credit”) is fine, but it can open you up to unnecessary back-and-forth or legal gray areas if phrased wrong.Best practice:Keep your criteria written down internally (income, credit, rental history, etc.).Apply those same standards to every applicant and keep a record of your process.When someone inquires, you can share your criteria in writing or over email so everyone gets the same info — that’s what shows consistency.If you want, I can share a quick example of a fair housing–friendly screening checklist I use with my clients, just message me and I’ll send it over.

As for the home office deduction, that’s a gray area for landlords unless your rental activity rises to the level of a business.You’re clearly trying to do things right, and I respect that.

This represents a gray area within the Internal Revenue Code, where taxpayers are currently able to realize certain benefits under the existing interpretation of the law.

@Briley Roe, sometimes there's confusion about flips being subject to capital gains vs ordinary income tax rates because the IRS doesn't automatically call it "flipping" or "dealer" income...you have to look at the facts and pattern.You're in a gray area, but based of what you described (4 properties sold in 12 months for $270K profit), the IRS could view this as a trade or business, not long-term investing.