I lived in Jamaica Plain
Which I enjoyed well enough; watching bands and drinking in the basement of Deep Thoughts was an important part of my mid-20s. Cambridge and Somerville are alright - most of my friends and co-workers lived that way, so I spent a lot of my time over there. Some of the ethnic enclaves - like the Haitian and Vietnamese communities in Dorchester - are interesting, but felt so removed from everything else.
There was (is?) definitely a lot of cool *stuff* in Boston - great film scene, some of my favorite restaurants and bars in the world (Sarma, Back Bar) - but in terms of places I actually want to *live* Boston is far down the list.