Do you mean, advice & suggestions about Boston, or living aboard in winter in general? There's some great threads in the archives of this subforum about winter living issueslike water supply, pumpouts, prepping your boat, condensation, heating, insulation. Check them out - and if you still have questions I'm sure those of us crazy enough to live aboard where the snow flies could answer them - no extra charge for the cheap wisecracks.
We've completed 4 winters aboard in the Chesapeake - absolutely love living on the boat. You're right, the liveaboard community can be awesome, and there's a tight cameraderie among those who survive the desolate snowy months together.