I think Rio is the best, but be prepared to pay the piper. Rio de Janeiro - Amo O Rio e Beleza!

Seriously, Rio captured my heart in the summer of 2000. But unfortunately petty theft, assualts and random violence plagues the city...and this is very sad. I'm a victim of all three, but I keep going back. Chris, Floripa in the winter is much colder than Florida, and there is humidy unlike So Cal. I would never live in Sao Paulo, maybe Santos. Floripa's real estate is way overpriced then tack on the Gringo Tax and you'll really get screwed unless you know the lingo and insider trustworthy friends!

Best weather [IMHO]:
1. South/Central Coastal California
2. Florida [November-April]
3. Medellin/Pereira, Colombia / San Jose, Costa Rica
4. Rio de Janeiro
5. Cartagena, Colombia / NE Brazil / Dominican Republic
6. South Brazil