House hacking in Boston or Cambridge, Somerville

[Jarrod Kohl]

Hello BP community!

So I have been around the forums for a while, and have been flipping houses all over Massachusetts, though the last few have been on Cape Cod. I am looking to pause on the flips and sink some money into some more buy and hold. 

Long story short, I have a connection who is open to selling some of their multifamily properties (they have a big portfolio) and although I am used to doing more value add investment these are all a lot more turnkey, which is probably a plus for the family and they have nice finishes.

One concern is that rents in parts of Boston have dropped 12% and I have seen individual rentals going for way under asking. To mitigate that, I have narrowed my choices down to about 3 properties which are mostly fully rented, but with 1 unit available. (aka 2/3 full) The big risk is with rents being as unstable as they are, how would you price them for forecasting. The benefit of the idea of house hacking is that I could take on more risk than normal assuming that even at way under current rents, I could still be "cashflowing"

The other benefit of doing it this way in Boston or Cambridge is to benefit from the new(ish) rules about Airbnb. The caveat with STR in MA is that as an owner occupier you have a lot more leeway to rent out the other units in your building. Though it has been hard to find something like this, now that I have a few to choose from I feel some analysis paralysis.

So the question is: Should I focus on the mostly full with one vacant? Or just look for the best overall deal and worry about renting the other units either STR or long term later?