OP, I forgot to say that I have lived in the Boston area since 1978 save 5 years in Manhattan and winters in recent years in Sausalito. Commuting here is unpleasant. I don't do it -- I started my own firm and our office is in a building roughly 1/4 mile from my house in one of the Western suburbs. The houses here are very expensive but the admin staff typically live in towns to the west of us and the cost of these drops off significantly with some distance.

My impression is that commuting on the Red Line is generally pretty good (snow may be a problem). So, if I were going to be working along the Red Line, I might seek a place in Somerville or at the other end (Braintree or Quincy I guess but I don't know that part of the world well) and send my kids to private schools. I can't comment on TheBOSman's evaluation of the equipment (but people who are in the know tell me that TheBOSman is right that the agency is a complete disaster). If the office is near North or South stations, as someone mentioned, you can take commuter rail. Neighbors of mine do it every day. I really like driving my car, but rush hour driving in Boston seems pretty gruesome to me. Lots of traffic, rude drivers, bad weather, ... .

If your office is in the suburbs, life might be simpler. Commuting by car could be pretty easy depending upon your location. For example, if the office is in Waltham (where there are pharma, tech and financial firms), you could live in Lincoln, Sudbury, Concord or Wayland where the public schools are very good and the commute might not be that bad. If the office is in Burlington, you could look to suburbs nearer Burlington, like Winchester or maybe Andover (don't know its schools).