Honestly if you are going to be driving it in Boston often I wouldn't buy anything very nice because A) it's liable to get broken into, B) you're likely to trade paint with dozens of other cars, and C) the roads in Massachusetts are terrible with pot holes. You'll want a small car if you want to park anywhere too
I wouldn't worry too much about the winter aspect of it, Boston doesn't usually get that much snow in the winter. The best thing to do is a get a set of winter tires, that will make a big difference no matter what the setup of the car or truck.
I live in New Hampshire where the winters are worse and with winter tires on my tiny FWD Saturn I've never had any trouble