I salute your plan.
What countries in particular are you talking about?
Among others
Thailand, though too many European expats have the same idea. I have a friend I grew up with in Chang Mai. He works six weeks a year in Australia, and spends the rest of the year with his Thai wife and her extended family on the land he has. Also have a Scottish friend I know through trading, retired from being a commercial fisherman and now lives on the beach a few hours south of Bangkok. He lives extremely well on less than $2K a month, extremely well. Tourist area's are too expensive, but he prefers living among the locals
Vietnam. Close Asian American friend of mine made his millions in the dot com era, retired to Thailand at 35 in the early 2000's. He tells me Vietnam is what Thailand was like 25 years ago. Cannot buy land, but can get long term leases, up to 99 years in some cases, my buddy is currently spending 9 months a year there.
Sri Lanka, and the south east coast of India, south of Chennai. Maldives are attractive, but perhaps too remote.
I have friends who live in Singapore who intend retiring in the Philipines or Malaysia. Not sure I can wrap my head around living in a muslim majority country though, but I plan to visit first before striking it off the list
Further down the list of places still to visit and explore
Madagascar, I grew up in South Africa, and my grand parents visited and bought land in Madagascar in the 70's. Extreme poverty, but extremely beautiful, and they never feared for their safety, and were so well treated by the locals - bit far from anywhere though, requiring connections through South Africa (I plan never to set foot there again if at all possible) or Seychelles to Europe
Solomon Islands, Papua New Guinea. Not a fan on all the Aussies expats, and the security situation out of the cities and tourist area's is not great.
Hainan island is China's version of Florida, just without the meth and Florida man. Not high on the list to be honest, but when I head to SE Asia next I am at least going to visit.
I lived in the Caribbean for 5 years in the early 90's, loved it, but it is like constantly living in a tourist trap town over run with fat cruise ship passengers, and the annual threat of hurricanes, and generally low standard of living outside the exBrit colonies - not interested. Belize and British Guyana are appealing, but I need to visit first. The ABC islands are attractive, but I really want some land, and that becomes expensive on any island, especially any with direct flights from the US and / or Europe
Having lived in Colorado longer than anywhere else in my life, don't get me wrong I love it here, and am fortunate not to have to deal with the liberal shithole cities, so good chance I don't sell our place in the foothills, I was recently approached about a 5 year lease. But time to move somewhere warm, green, and on the beach.
Spend the days kiteboarding, and swinging from a hammock. Trade for 90 mins when the NYSE opens (makes Belize and Guyana attractive), but the guys in Thailand and Vietnam can get it done even with the time difference so it is possible.
Open to suggestions though, it will be more fun to visit these places and come up with a real short list. The actual divesting and moving will suck.