I'm also in Mass and my son just got licensed this past September. The comments about FWD and snow tires, while would be OK, wouldn't normally cut it with the winters here, combined with the roads and hills. Can you get around without 4WD or AWD, sure, but I'd personally prefer having 4WD/AWD.
Anyway, if you have a friend or family member that has half a clue about cars, ask them to assist with the search (or at least take a look when you find something that might fit). I had my son narrow down to different vehicles that he thought he'd like. We told him we would match any monies he put up. That way, he has a vested interest in it, and treat it well. As a 16 year old male, he of course looked at everything the least practical for our area. Rear wheel drive sports cars to be specific. That didn't happen. He wanted my wife's car (a 2014 BWM 328i X-drive). Oddly enough, we considered that because it's a great sedan, AWD, very reliable and surprisingly "affordable". However, Her car is in great shape, and I anticipate some growing pains so I wanted him in something a little less nice or that could a little bumping and bruising. He opted for a Jeep Wrangler. I was good with that choice for a few reason.... it's 4WD, it's compact enough for him to learn how to maneuver in traffic, parking, etc, it's slow (not a lot of power), and he can have fun in the summer too removing the top. I'm a car nut, so I was able to find a few, check them out and narrow it down to one or two. He wanted a (newer) 4 door Wrangler, but they were out of his price range. I was able to find that diamond in the rough.... 2004 with a 4.0 motor, automatic transmission (I did want him to get a manual), hard top AND soft top, full doors AND half doors, ALL service records, all original parts (prior owner upgraded some parts to better quality, and saved the OEM stuff), 80k miles on it, and spotless. He fell in love with it, which helped because I knew he'd take care of it. We got it for $8000, of which he paid $4000. He also bought his "mods" and worked with me on other changes he wanted to do. His sense of pride in HIS Jeep really shows, and that carries into how he takes care of it.
When we bought it, stock (after I detailed it for him).
He's since added bigger tires and different wheels. He's also changed up the interior too (I did help a little, but mostly showed him how and he did it himself). Here he is, the day he passed and got his license...
