After trying out life in various places I've made what is likely to be my final choice. (never say never though)
I now have my home base in the Okanagan Valley in British Columbia, Canada. Most TT posters probably won't even know a thing about it.
It has the warmest, driest climate in Canada. With only 12 inches of precipitation per year it is a desert region, yes, Canada has a desert. The desert portion in the very south end of the valley is where I live. In summer it can reach 40c but temperatures in the 30s are the norm. In winter it can hit -15c but -5 is the norm and the occassional snow we receive is never more than an inch or two with a 1/4 to 1/2 inch per snowfall being the norm. So there are 4 definite seasons with 3 of them being relatively warm and the winter being relatively mild. I think last year it rained 3 or 4 times from May through September and never for more than an hour or so.
More important to me however is the DRY part of the equation. Dry means low humidity. Humidity is something not a lot of people think about but it is humidity that makes warm temperatures feel uncomfortable and it is also humidity that makes cold temperatures feel damp. When I lived in the UK, damp was a year round reality.
The valley runs around 100 miles from south to north and is mainly orchards and vineyards. All watered from the river and series of lakes that run down the middle between mountains on both sides of the valley. The mountains are the reason why the valley has its own micro-climate.
For hiking, fishing, wildlife and any kind of outdoor activity the valley is a paradise. For major city attractions, Kelowna, near the middle of the valley has a reasonable amount. It also has the second highest house prices in Canada.
Canada of course has one of the best infrastructures in the world, which becomes more important as you age, particularly health care.
The only downside really from my point of view is the access to easy and economical travel. It is a 5 hour drive to Vancouver or 3.5 hour drive to Spokane, to access a major airport with good international connections.
I think most people think in terms of 'fantasy' when pondering a question like this one NOMAD but those who have already lived in 'fantasty' locations will give very different answers for very real reasons. Living in a beach shack on some Pacific 'paradise' island sounds great when you say it fast but the reality soon becomes apparent when you've lived on one for a little while.