I'm from the US Southwest and live in Thailand, up country .. and will probably stay until I die. The biggest negative for webmasters might be fast broadband access. The larger cities have good BB (4-10 meg .. sometimes), but it's not up to Korean or western standards. Also, being a loner, I tend to avoid tourist areas.
There is a fair amount of red tape for establishing and operating a business, but easier for "under the radar" on Non Immigrant "O" Visas .. (one year at a time with multiple entries) .. "B" visas might be better.
Beaches and mountain scenery is great. Food is outstanding. Outside the tourist areas, people are terrific. (repeat: avoid most major tourist areas). Language can be a problem, but people are extremely helpful if you make an effort.
A nice 2 BR condo in Cha am at the beach (2 hr south of BKK) can be had for about Bt 5 mil (about 150K US), no property taxes.
Oddly, not a good place for freelance coders .. expensive and like to work for companies .. social.
WARNING: Thailand seduces and destroys lives .. proceed with caution.
If I ever decide to leave, my options would be:
Chile (Arica or La Serena)