... andhow about "Upstate New York"

[torquer]

A number of the places named in this thread are college towns, which New York state has in abundance. College towns are often cited as good places to retire: diversity, range of cultural offerings, higher level of public support for institutions (educational, sure, but also medical, which retirees especially benefit from.)
Downside is higher local taxes to pay for all this, but OP outlined mitigations for NYS pensioners. Also, especially at commuter schools, more traffic, often on marginal access roads, so that impacts riding. But summers are better.
So on balance, if I were relocating (and Tuscany or Maui didn't work out) I'd start within site of an ivory tower.