OK, I'm still Chile curious. The visa is significantly easier than Peru and it can be done all from Thailand. Plus there are lawyers, etc. to make it even easier. I'm sure not cheap but maybe worth it. I still don't understand the taxation as far as social security and withdrawals from IRA. Your country might have a tax treaty with Chile. THe USA doesn't. So that could be a deal breaker. As far as health, it's probable to be able to get on the public system and even if paying private it's going to be cheaper outside Santiago. Now I've found a city that could be better than Vina del Mar for my retirement purposes. La Serena. Why? Smaller sized city 200K ish but still has most of what you need. Seriously cheap rents. Good choice of neighborhoods. Seaside, central downtown. More residential. You DO NOT need a car (except in an outskirts area). Central area very walkable even to a modern shopping mall. Very nice weather. Not humid as near to the desert. Unlike Vina del Mar the ocean water while still chilly is swimmable in summer (think Santa Cruz, California). Food scene? Well not sure. There are Chinese restaurants, not sure how good. The local food features great fresh seafood and that's hard to mess up. Plus of course the always promising Peruvian restaurants. Not super exciting. On the boring calm side. But as you get older, it's that what you really want and need? Video in Portuguese but turn on English subtitles:
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