> The problem so far hasn't been finding a country that is more hospitable than the USA, but in selecting from the dozen or so who are more hospitable, and trying to figure out which one is the most hospitable.
Can you list the dozen you are considering if not the complete thought process? Are you considering perhaps places in Asia like Thailand and Singapore?
My list will be different than yours. I do recommend Chile. Thailand and Singapore I haven't visited, but both have their appeal. Thailand's limit is that you can't easily get residency (as I understand it) and so you have to do the border hop every 90 days. Singapore is efficient and by the book, which means if their residency programs work for you, then they could be really good. The country is a bit rigid, so might want to visit to make sure its right for you.
I'm assuming you're talking about tourist visas, with that "90 days border hops" (single entry).
Working in Thailand on such tourist visa is illegal. Getting a business visa (and thus work permit) is not easy at all. Foreigners are not allowed to hold majority in a Thai company (just as they are not allowed to own land in Thailand). Thailand is a very xenophobic country, and its laws reflect that.
Working around the visa system illegally is not difficult, and many people do that (incl. IT freelancers). But contrary to the popular image of a "care-free tropical paradise", Thailand is one of the more difficult choices to run business in/from.
> The problem so far hasn't been finding a country that is more hospitable than the USA, but in selecting from the dozen or so who are more hospitable, and trying to figure out which one is the most hospitable.
Can you list the dozen you are considering if not the complete thought process? Are you considering perhaps places in Asia like Thailand and Singapore?