[ramchip]

Aren't you extremely wealthy compared to the average Thai?

It sounds interesting for someone in your kind of situation, but there's a lot of assumptions that are not universals: being fairly rich (or having skills worth a lot) off the start, being limited to cheap countries (the parent poster talked about going around the world, which sounds a lot more expensive than and quite different from staying on a beach in Thailand), having skills that can be applied via teleworking and short contracts, etc.