My best friend from HS now lives in Sao Paulo! The most conservative guy ever and yet he chose to live there. He was reading Ayn Rand in Jr. High, if that tells you anything. So I couldn’t see him selling everything off and moving to socialist Club Med, but he did. I guess when you have enough money to retire at 40, anywhere is probably a nice place. He abandoned the US in 2009 post Obama and has no regrets. Chatting online on election night all he could do was tell me “Told ya so”. He now has several hobby businesses, employs locals and runs a cash based/underground mini-empire, but mainly lives off his previous investments and sale of business here in the states. Pays zero taxes, but claims makes up for them in friendly bribes to friendly officials. The the Brazil way. He enjoys the freedom, the lifestyle, and yes, the women.
So, based on my very limited knowledge, Brazil would be great if you already have oodles of money.
I'm surprised that your friend didn't choose Buzios or Fernando Noronha. It's better to live near the beach if you ate independently wealthy.