My wife and I owned properties in two different countries - the UK and Florida - and did the exact opposite of you.
The older we got the less inclined we were to deal with the hassle and worry of a second property thousands of miles away.
Especially - as this week is illustrating - in a hurricane region.
We sold up and now spend our winters travelling to different countries.
Health and medical issues also become more pressing as you advance into the twilight years (😂)
We've also encountered many couples who've bought a second home in a place they vacation in but after a few longer trips the attraction pales and the home becomes just another holiday rental/AirBnB which means it's rented out at peak times which is when the owners originally wanted to stay...
It's entirely a subjective opinion but if you can afford a million on a vacation home you can afford some really nice winter stays - and when they're finished you pack up and move on without a second thought and leave the insurance, maintenance and HOA bills to the owner.
Consider also home exchange. We have a small place in Ireland we bought years ago in my wife's home town, about an hour's flight from the UK.
We use it to visit her folks and the rest of the time have it as a home exchange. We've made 25 exchanges so far and visited countries including the USA ( Florida every year ), the Caribbean ( including our forthcoming visit to SXM ) Mexico,Thailand,Bali,Vietnam,Cambodia and Australia. Totally hassle-free. Our two-week stay on Simpson Bay is essentially costing us nothing but the air fare.
www.homeexchange.com is the biggest and best website to deal with.
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