I don't know what Thailand's like outside of Bangkok. Fairly rural? I have no idea. I had a few weeks in central Bangkok and decided it was essentially an overgrown country town. But great for food.
Ideally, I'd like a beach. And a view. And restaurants. About the last thing I like is cooking for myself. There has to be good, cheap, simple restaurants. Thailand has those, I know. I think probably Asia is where I'll stay. I could see myself in Europe, maybe. The Americas is another adventure and it might work well, but the prospect is more immediately daunting than it is retiring.
I grew up near the ocean (on the edge of a city that might reasonably be called a giant suburb, which I still find claustrophobic every time I visit, it's clean and varied but somehow spartan and empty, though the water is great and the air far more expansive than here), and wouldn't mind living near water again. But modern communications infrastructure at least is important to me, as is some ability to get around by myself.
So, things to see, a place to eat, some hot sun and humidity, some water, and some high speed internet. And something to do.
I'm 46. I probably have to work another twenty years.
But I was actually thinking, I could go do all this right now. If you really can do this on about 1200USD a month, I could kick back for a year or three. I'd be broke after that, but perhaps a rich lady would marry me for my wealth of knowledges.