I've been working almost entirely remote (some occasional short periods of going to a small office with clients) for about 12 years.

For most of it, I've been living in Thailand (almost 8 years). Lifestyle here is pretty laid back, but you need to be more aware of your own/your family's safety, in a whole lot of different ways. It's also not particularly easy on foreigners if you want to run a company here, but it's doable. I believe Americans will have a slightly easier time with this, due to an agreement between the countries.

There is a somewhat-formed plan for us to move back to Australia at some point, and we'll almost certainly end up somewhere outside of the major cities, probably one of the larger towns in Victoria.