From what I see, many countries don’t easily issue work visas unless you have a sponsor in the country, so I wonder how legal being a “working nomad” is.
I feel that working for overseas on visa-waiver programs is sort of in a gray area but I doubt that the people at the customs would easily let you in if they knew you were technically going to work in their country.
How do you handle this? Do you get a work visa for every country you visit?
What if at the port of entry they ask you “what were you doing for three months in Country X without a visa?” “Uhm… vacation… and I’m going to be on vacation for three more months here.”
I’m thinking of spending the next three months in the US and this possible questioning is worrisome.