I'm from the near Boston. I can give a couple quick things to make your game seem more local.
Some geography. The coastal area North of Boston is called the North Shore. The area South of Boston before you hit Cape Cod is the South Shore. You call Cape Cod, "The Cape."
There are a bunch of towns that get clumped in with Boston. You can call the collective Boston, or the downtown area Boston, but when being specific, you can name the particular towns. ("Yeah, I live in Boston." "Which part?" "Somerville.")
A lot of the buildings are old. Most of the roads are as old or older. The result is that a lot of neighborhoods are really crowded.
Speaking of roads... it's kind of Hell to drive in Boston. Most of the roads are one way. The majority of them are far too narrow. Oh, and construction projects constantly spring up without warning and reroute the traffic in whole areas. You'd be better off parking and either walking or taking the T (what we call the transit system), but good luck finding parking, especially if you're near Fenway and it's a game night.
Speaking of the T, Boston has a public transit system. There are only four subway lines, but those will get you within a couple of blocks of most places downtown and many central places in the surrounding areas. A fairly extensive system of buses fills in much of the rest. Rail and bus lines leave North and South Stations, connecting with other cities in and out of state.
