Tough choice, not overly knowledgeable about either. Everyone who has ever visited Boston says it's awesome. Not a fan of NOVA/DC in general from my visits to see my aunt, but I have heard Virginia Beach and Richmond are both quite nice. Then again, Cape Cod is pretty much a more commercialized, bigger Door County, so ... I don't know, LOL.
Lean MA.
Eh, no. Not unless you're a fan of corrupt police departments, drive-by shootings, and robbery.
Although there is (supposedly) a pot dealer on every block if you're looking for that.
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