Thailand is ok, but there are limits to what you can get out of the experience imo. It's a very uniform country culturally, with very little individuality. It's a great place for learning your ways as an expat or digital nomad for the first time. You can party, dive, train muay thai, bang feminine girls and live comfortably much cheaper than elsewhere. Good fun for the first year. Then it gets a bit bland and boring.
I loved Japan when I was there, but it is a very closed society and not at all set up for entrepreneurs or foreign business. It is also very expensive. Still, amazing and rich culture and tons of individuality and subcultures. So much to explore to last a lifetime. It is the only country outside Europe I've been to where you get the feeling of a culture that can match the old europeans. Japanese people are very friendly and if you like feminine women who can express themselves, then you're going to like it. They lack the inherent sexyness of SEA girls imo though.
Philippines is not for the beginner in my opinion. It is actually in many ways preferable to Thailand, but the poverty is very real and it is not safe.
I've heard many good things about Bali, seems to be popular with quite a few online people. Could become a bit of a hub for location independent biz.
Taiwan is the dark horse and I've been seriously considering checking it out. It has a tropical climate but much higher standards of living than the other tropical asian countries (not counting Singapore). Relatively unspoiled by mass tourism and sex crazed english teachers.
China of course is also an option, but I don't know much. Shanghai and Beijing are basically western cities with large expat population and prices and attitudes to match.
That's my opinion on Asia. If I were an american, I'd probably rather check out south america, central america or the carribean first.
