I’m also about to retire.
The analysis is different for a retirement home.
On retiring, we aren’t raising children, we are just (to put it bluntly) waiting for death.
There is a rather short time horizon in this calculation.
Will it be reasonably good for X years? For any given place, probably yes. And if it goes bad, I at least am expendable. What is one old man more or less?
I find Europe, especially Southern Europe, a better choice. You have, besides much cheaper cost of living for a similar environment to the upscale urban islands of the US (SF Bay Area, New York), plus easy and very affordable transportation to an endless range of places that you cannot hope see in a lifetime.
I live in Spain, a short walk from the beach in an area with darn near perfect weather. Costs me $2000 Euros/year for health insurance for my wife and myself (it used to be $1800 but we just had a price increase due to an age jump). I am eligible to collect SS but I haven't started yet because cost of living is low enough for us to live on my wife's British pension alone. My wife came here by herself on a house hunting trip in January of 2016 and she felt so safe and comfortable walking around by herself, even at night, that we bought a house that week and were in Spain permanently by March. You can always send me a private message if you have any questions on retiring there. This is the view we wake up to every morning
