Just this AM I had a call with a citizenship by investment firm (happy to make recommendations in this space as I know a few people through previous work) and we were talking about tax implications for remote workers and various programs. All I can say is, get ready to pay an accountant a lot of money. If you want the simplest break as an American, I would leave the U.S. on Dec 31 this year and go establish physical residency somewhere with no local income tax (or via a program like Barbados Welcome Stamp) and stay there long enough to pass the smell test (e.g. open a local bank account, have an address for a few months)... should be at least 3 months, probably more like 184 days. Then you can move on and go other places (not the US) for under 2-3 months at a time, not creating roots. Of course there will still be complications if you're doing this while employed somewhere but I guess if you're an independent contractor or with your own company you can spin up an overseas entity somewhere.