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Brattleboro of course! Great town, even though it hasn't quite rebounded from the hurricane.
Keene is in NH which is a sea of libertarianism (puke) economically supported by the Mass economy.
Ocracoke NH or Provincetown MA?
The only Ocracoke is in NC. I'd pick Provincetown, as its connected to the mainland by car. Ocracoke is in a bad spot for potential hurricane impacts and its associated sea level rise impacts due to climate change. You can even take the ferry in P-Town to Boston as well, and it has an actual town center with historic buildings and a lighthouse of its own. It even has a full-service supermarket (Stop & Shop) as well.
Highrise in Manhattan. If I can afford that, I am sure Ill know plenty of people who have second homes in the Hamptons to visit.
Bethlehem, PA or Wichita, KS
Bethlehem. Kansas' largest city (but not its largest metro) punches below its weight. Not to mention that Bethlehem has managed to do some really creative things with its old steel mills, like turn one into a performing arts center.
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