Is Martha's Vinyard a Good Neighbourhood?

 Sure it's better than NYC or LA, but [better than Detroit] doesn't mean good. This isn't a high bar. 

 What is it like living in Martha's Vinyard?

 Most likely, it's an enormous pain in the ass. Your neighbours are all massive cunts who won't leave you alone. Wall-to-wall Stepford smiles. Everyone in a ten-mile radius, instead of asking what you do for work, will ask you about your "favourite" "cause" and then ""suggest"" you donate to the NGO their daughter works for. Doubtless there are "welcoming" community events which are interminable speeches denouncing farmers and oilworkers. Here "welcoming" means [mandatory]. Or they'll find your investments and short-sell them. Good luck paying your taxes, lol.

 On top of this, naturally getting rich enough to afford a place there attracts the attention of the government. Regular meetings with regulators lest they feel snubbed. Lots of jizyas to pay.  

 Yes, you can manage it. The hassle can be minimized. They're all desperately vulnerable to manipulation, although you'll have to manipulate them repeatedly to maintain it. The way I had to perform mind-control maintenance on my teachers at school. 

 Of course there's also the assassination problem. Awfully high "accident" rate on that island. How peculiar. You probably won't be targeted, but is [probably] good enough for you? What if an assassin gets bored during a slow quarter? 

 Better than Detroit doesn't mean good.  This is not a place to be envious of. The problem with Martha's Vinyard is that it's full of Marthas.