There are a lot of great things about living in the US IMO, but if you can truly work from a home office anywhere in the world, there are some exciting options out there with favorable visa and tax considerations.
I love the Caribbean but I would be wary of island fever if I actually lived on one of the islands.
The working vacation idea is a great idea. Hell, you could take 2 or 3 of those every year and be a citizen of the world.
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