First, renting in the Boston area is horribly expensive. My one bed/1 bath which was $1300 (plus utilities!) a couple years back is now going for $1600+, and this is in North Reading!
My advice is to rent from an owner as opposed to a big complex with guaranteed rental increases every year. Tons of people are looking to rent their condos, etc since they aren't selling very well (or they are underwater).
Next, places inside of the 95/128 loop are generally more expensive than outside. Outside of 495 is cheaper yet, so you can look into Chelmsford or Billerica. I have friends who live in Woburn, its nice enough, but it really depends on what you're looking for.
Cambridge and Somerville are essentially college towns and have a younger demographic and tons of stuff to do every night. Commuting out of that area is horrible though, even if you have a reverse commute since its basically back roads to the highway, just FYI. If you can take the T/Commuter rail to your office then that would alleviate that particular issue.
Winters are too bad, I would invest in a small shovel for your car for when you get snowed/plowed in and a good set of gloves, but other than that you should be fine. I moved up from Houston TX and have been fine.
I know nothing about the weapons laws around here.
