No due to US government and the high cost of flights to most of the world where stuff actually happens. Also, 'remote worker' hangouts tend to attract posers rather than doers.
Agreed, US is probably one of the worst places to work remotely. Even if you want the region, Canada or Central/South Americas are probably better choices. Maybe Chile.
That depends on your citizenship. If you are a US citizen be prepared to report all you money and income tax them when you are abroad. Oh, and also you may be denied a bank account by virtue of your US citizenship.
As someone not currently in a position to experience one, that's disappointing to hear.