One can save a lot of money living in a lower cost place and then traveling with the dollars not spent on some luxo condo somewhere. The weather at lower cost placed is usually fine for 5-6 months out of the year. Get nearish a reasonable airport. Figure the things you enjoy doing, golf, bridge, concerts, whatever. But walk a lot.
I had this discussion on line with a coworker a while back, he's a high level VP now retired, money for him would not be an issue at all. And he's very smart, a Purdue grad and patent lawyer. He doesn't play golf. I should call him now that he's retired, he told me he has kids and grandkids in the Cincy area and probably would stay put. Another good friend is French but lived in Cincy six years in a nice place, was CEO of a pretty large company there, neat guy. He returned to France because of grandkids. He told me he would prefer otherwise to stay in the States. They own a nice house in a small village about 100 km outside Paris. He doesn't like how France is changing, but he's kind of stuck.
In our case, our kids are scattered, mostly on the west coast now, but one in C-bus and one in France. They come here sometimes, we go there, etc. We have a large airport 10 miles to the south of course with a subway link.
My wife has a few places she likes to revisit, Hawaii being one. I'm encouraging her to be more adventurous, and she's amenable mostly. She has old friends all over Europe she wants to visit.
One thing we did before moving here was travel around the US a fair bit and ponder if living HERE would work, we looked for condos and houses and various and sundry, Vegas, Austin, Jacksonville, Tennessee, California, North Carolina ... I was maybe overly concerned with taxes, but it worked out.
