It depends on the country. I lived in NZ for a while and they are notably resistant to foreigners, which after being there I can understand. There aren't "loopholes" per se, there are countries happy to take in pensioners, with Portugal and Panama among them, as well as Mexico. If you are in the search, the author to read is Tim Leffel. He specializes in researching ex-pat destinations and updates his book every two years. He's a friend and I write for his travel website. That is where I got the ideas. No loopholes. Just research. I agree that it may not be in the cards for everyone, for what we have to give up is for many folks just too much. That said, there are places where you can, but your expectations will have to be managed accordingly. If people expect to live the American lifestyle in a developing country, they will be very unhappy indeed. That was part of my point.