Ask HN: Working remote US job from random countries?

Does anyone have experience working a remote US job while going around and living in various countries? My girlfriend and I are interested in trying this lifestyle for 3-6 months after our current lease runs out. We are mainly sick of the car culture in the US and enjoy living in places built for humans.

We are early-mid 30s with no kids, no house, no pets, and no real obligations besides my remote job based in the US.

Are there legal implications with work, visas, etc. or any interesting loopholes to consider? Would really appreciate any insight or even reasons why this might be a dumb idea.

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