The problem with this is that either you need to be retired, or have a job you can do (or busines you can operate) while travelling according to the seasons. My job requires me to have a fixed place of business where I am present. My job also requires mastery of the local language of business - which limits me to French and English speaking cities. This rules out most of the places I have loved as vacation sites. I also have come to enjoy and expect a certain level of material comfort.
Paris was great to visit, but unless you have lots of cash, you'll be living in a small apartment. Toronto may be expensive, but Paris is more expensive, and my inquiries a few years back led me to believe that without established contacts in the city, you'll be hardpressed to find a high-paying job that would affored you the lifestyle you enjoy in Toronto or any other large Canadian city.
I loved southern Spain, but the economy is in the shitter - tourism is the only thing they have going (and that has collapsed). In any case I'm not in the vacation condo construction business or the hotel business and I'd anticipate having a very hard time earning a living there.
I could earn a good living in any of the Caribbean tax havens. But I don't care for hurricane season and I don't like working for tax cheats.
New Zealand is beautiful, but they regularly lag well behind Australia in economic performance. I don't know how they are dealing with today's crises, but during their downturn 20 years ago, the job market was more or less closed to foreigners. Now if you are coming in with enough cash to support yourself or you are starting a business, NZ could be promising. If you're looking to draw a paycheque from an employer, it may not be the best move.
This is why my choice would be
Dallas TX - (in a few years, once the economy has recovered)
Winters are shorter and milder. Good economic opportunity (I expect oil to be booming once the economy recovers). No state income tax. Decent sports town (although I hate the Cowboys).
