STR is another concern, many towns have laws against it but most towns do not enforce these laws, just make sure you are aware of them becuase they can be enforced. 

@John Matthew Johnston 80% of the time, it's a thankless job:(You're never fast enough for complaining tenants, nor fast enough or cheap enough for owners.To have any chance of success, you have to be extremely organized, or every day starts with your hair on fire!

And when you’re in an extremely tenant friendly state such as Colorado, this can be a nightmare situation. 

Ethical ConsiderationsYour concern about ethics is valid and shows you’re approaching this with integrity.

More concerning is the new Florida-based entity, Themed STR Capital Fund, set to launch in 2025, for which Santarelli is a fund manager.

Also keep in mind that if the concern is lawsuits, they can still name you individually in a suit and it is just another battle.

The deal can make sense even if it doesn't meet some arbitrary "rule"  Thanks for the insight, everything you guys are saying has been extremely helpful.

My concern is whether I’d then be locked into only larger deals in the future. 

If you haven’t already, make sure you’ve documented everything thoroughly—photos, messages, invoices—and highlight the guest’s negligence, like leaving windows and doors open in extreme weather.If you haven’t heard back after asking to escalate, follow up again and politely but firmly request that a senior claims specialist review the case.

The problem is that you don't get an opportunity to do an inspection before you buy.If you buy pre-sale from the owner, you have arrears to bring current, getting the owner to move after you have solved their problem and taken the pressure off, along with the previously listed concerns.