Hello! I used to live in Federal Hill and more recently have spent time commuting from Gloucester, MA to work in Boston which is an identical distance - about 1.5-2 hours each way. It takes me ~25 minutes (carpool) to get to the commuter rail, about an hour on the commuter rail, and about ~25 minutes on a bus/subway to get to work from the train station.

It’s not lovely, but if you’re only doing it a few times a week NOT everyday it IS doable. The train is pretty relaxed, and I generally listen to books on tape which is enjoyable. It’s doable - but I will say in your case I’d recommend it only if you’re close to South Station. If you have to take multiple trains or busses to get to south station, all the connections will truly be terrible. One mode of transportation for each leg of the journey is (to me) ok.

Another thing to consider is how long would you plan to have this job? Is it just for a few years? More long-term? That may help you decide. Good luck!