Ah, but a signature can be changed easily...
Massachusetts is actually pretty nice, I like it better than Florida, but I was only 21 when I left and hadn't really 'experienced' Florida much. I at least like the environment better, I like the weather. Taxes are hell, but I also make much more money.
I'd never suggest taking the highway the entire way to Logan. I've never done it, and when I'm in the car with my ex-gf's father when he does it I fear for my life.
I'd take 495 North to I93, then get on the train at Wellington Station.

Of course that's if I wasn't able to take the commuter rail, which I'd do if I was working at Logan.
I'd never even seen a subway or commuter train before I moved here, let alone ridden one. I was in awe by the fact that I could park at one station, then ride into another station near the airport, and take a bus ride into the actual airport.