@Cheryl Crockett  If a lawyer's opinion contradicts the actual state law, that lawyer is giving you bad advice and his opinion is worthless.MA state law is crystal clear. 

Treat your partnership as a formal company, do the due process, have stuff in writing... don't make the decitions and stuff personal, is a business transaction in which the common goal is an entity of itself separated from you as individuals....Partnerships are good, they bring synergies and potentiate your growth, but be thorough, crystal clear and put EVERYTHING in writing, words (opinions, verbal compromises, intentions... etc.) are worthless when S** hits de fan

The condo buildings that do allow STR are mostly going to be condo-hotels (think W Hotel, Roney Palace, 1 Hotel, etc.) and these buildings do not qualify for conventional financing.

That said; my crystal ball is broken.

It sounds like you've already done so, but be crystal clear regarding what you want to do (ie: have the end-game plan before purchasing) and receive confirmation with your contact at the city that everything falls within the zoning regulations.

I know out here in East TN you get a voucher which covers $X amount, and if you find a place for more than that you have to cover the difference yourself, the caveat being that the total you pay in rent cannot exceed some percentage of your available income - i.e. they're not going to give you a voucher that you can then use to go live in a palace by paying the difference. 

Of course I disclose again before we go in (I make it crystal clear who I work for at the beginning of a conversation because it is a legal mindfield).

Your $205k property might come back crystal clear or might come back with $50k in necessary repairs.

In 2019 for example (just to use the Core Logic article since you may also have it open), we're talking about FHA loans having delinquency of 13%, while non-QM has about 2.5% for same.No crystal balls, but I don't see non-QM/DSCR being the harbinger of doom. 1) It's a small number of loans, and 2) it outperforms the FHA loans that haven't had major changes since well before 2008 (the 2005-2008 loans were far riskier even than today's FHA, no one blames FHA for 2008, and FHA at any point in the last 20 years is higher risk than today's DSCR/non-QM).

Does anyone have a short term rental in Crystal Rivers?