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So, if you are driving to work you want somewhere close to the hghway. Brookline and Somerville are great areas, but you want to go with roommate, living alone in Boston can be very $$$. My wife and I currently live in JP (Jamaica Plain), we love the area, has a real chill vibe, great bars... We are about 15 drive to the highway, 15 min T ride or so into Boston.
We pay for a two bedroom $1400, on street parking but no sticker needed. That is the other thing you need to find out is if you need a sticker for the area you are in. You may also want to look at Davis SQ, Union Sq, Cambridge area. These are all super fun areas...
Let me know if I can help in anyway.