It is full of Mass Investors who are always looking for deals

You would need to network with HR professionals in your market for referrals since they generally are the ones who arrange for those contracts.Do your homework...it would not be the play I would make.

The more systems you have in play, the quicker you can assess and make decisions.

@Jonathan Masse I would think with a 7 plex you could get a dumpster.

Househacking here isn't an income play; it's a wealth-building play.

Just from a pure market standpoint, your are going to be hard pressed to find worthwhile duplex/single family homes in your price range from Greater Worcester -> East Mass.

Also keep in mind depreciation plays into this, which you don't mention at all. 

I think you are playing in a dangerous situation if you go the hard money route.I also want to help give you realistic expectations.

If he has been doing it his way for almost 50 years there is a good chance he isn’t going to was to hear it frankly.That said, if you play along, even if you can’t use subtle techniques to move things along, you may win his trust and be given some buildings to manage- after which you can slowly change things.Above all else enjoy your time with him.

This will avoid issues down the road if she is flaky and using boyfriend to play the tenant game.