I was born and raised in the boston area. Spent 8 years working "downtown" in a few different locations.
I hate Boston. Everything about it.
Much of what others have said is true. The roads, the commutes, the people, the tourists, the cost of living, the home prices, the congestion/concentration...everybody is spot on.
New England is horrible because it's so inefficient due to the "historical charm" that nobody wants to disrupt. I wish somebody would come in and level the entire city of boston and start over with competent city planners.
Anyway, a few things to enjoy is that Boston (and surrounding cities) has done a lot over the last 10 years to focus on the arts, if you like that sort of thing. Also, being minutes from city/mountains/beaches/parks/hiking trails is a plus. From Boston, you can get to any of those in under 2 hours. Mountains of new Hampshire being the furthest out of that entire list at just about 2 hours. So there are plenty of options for a weekend road trip that most of the country has to plan a vacation to get to.
If you are a sports fan...lately, this is the place to be. Weather you like boston teams or not, it's a very vibrant culture here due to recent success over the last decade or so.
As for drinking and nights out, Boston has some good clubs and nightlife. Problem is they close early (bars kick you out at 12:30am essentially).
One drawback is that the public transportation BLOWS. Our subway system is a horrific mess. Use taxis.
It is very expensive here, so $83K I hate to say it, doesn't get you very far, but I don't know your style of living, so take that with a grain of salt. I live in a small 3 bedroom ranch in Rhode Island and I'm embarrassed by how much it cost for 1500 sq ft. I'm lucky to have a good size (half acre) lot with a nice yard for the kids, but again, I'm in Rhode Island where land is a bit more accessible than boston and it's 'burbs. Somebody pointed out that if you want a yard, prepare to commute an hour each way, and that's pretty true.
If you like thrifting and game hunting (which I know you do), it's a pretty good scene here. So many colleges here and parents are always cleaning out kids rooms and donating to thrift stores. I know that's similar around the country, but that is one way the concentration of people kind of helps. Game "stores" are atrocious here, but the thrifts are good.
Definitely some good things about this area, but Boston "proper" very much sucks.
And for the record Ark, the actual residents are not into the "pilgrim" thing as much as you think, that is a tourist draw and most people are fed up with it. Its like people in time square new York walking aimlessly with maps and selfie sticks. Think actual new Yorkers like that? HA!