[KSigkid]

mu_agd definitely gave some good pointers. Like she said, Brookline, Allston/Brighton and Fenway will probably be the best places to live for you, with Brookline being the most expensive. That is even more true if you're living alone. If you expect to pay at least $1000, you won't be too surprised by the rental prices. I would suggest starting to look at around May, as property dwindles pretty quickly as you get towards September.

Again, you definitely don't need a car, unless your job calls for you to hit the suburbs. Parking is very expensive, so I wouldn't suggest bringing a car unless you absolutely need one. The T can bring you most places you need to go, including all around Boston, to Cambridge, Braintree, Quincy, and Newton. Even after that, the buses and commuter rail can take you out to most of the burbs.

There really isn't one "style" in the city. Some people are preppy, some are more working-class, and some are all over the map. The bar scene is pretty laid back in most places, you can get away with a t-shirt and jeans. Some spots, though, you'll definitely have to kick it up a notch (dress pants, black shoes). The vibe depends on where you go; some places are laid back, while some are a little too self-important.

The job market has gotten better around here, but it's not easy to find a job. The best thing to do is start looking as early as possible, and work any connections you can find. This is especially true if you're looking for a specific job or a specific pay (to pay for living here). For philanthropy, there are a bunch of different places in town, but for many the pay is low, while for others they have small staffs. If you get more specific about which type of philanthropy you're looking at, I can probably give more detailed advice. (I've worked for two non-profits with sizeable charitable arms).

Definitely PM me if you'd like, or post any questions here. I love living in the Boston area and am always happy to help.

ETA: The city, overall is pretty safe, as long as you have common sense. There are some areas (Roxbury, Downtown Crossing) where you wouldn't want to do anything stupid, but overall as long as you pay attention you'll be fine. You probably shouldn't be waving your wallet around or threatening anyone, but you don't seem like the type to do anything like that.

Honestly, as a guy you'll be fine, but I know there are women who are more careful about things (carry pepper spray, don't go into certain areas, etc.) It's like anyplace else; don't make the wrong person angry, and you'll be fine.