Yup, all good points. We know about the tax issues with respect to Italy. If you spend more than 185 days there you're taxed at their rates, which are very, very high. We'd likely move back and forth between there and another country if we even decide to live there. If you're truly nomadic, then you have to "domicile" somewhere in the States, and I'm honestly not sure how that works. I know RVers like South Dakota for this purpose, where you can establish residency and get a P.O. Box in a 24 hour period, but not sure if that works for international nomads.
I saw that you mentioned Portugal in another post, and that's a popular spot for ex-pats these days. But, it's also driving up the price of real estate in some areas and making it less affordable than it once was. That's happened in Costa Rica as well, another place we have our eye on. But, we've only vacationed there once, and it was at very nice resorts, so not exactly "living like a local". It used to be quite cheap to live there, but now real estate prices, especially near the coast, are pretty high.
I think the FIRE movement and the digital nomad movement are a part of this push for even younger people looking to retire early or work remotely and live cheaply. It seems that Americans are always looking for the "next place" to go. I remember seeing that some Americans were buying pretty cheap ocean front homes in Ecuador in recent years. But in a country with an unsteady government, things can go south very quickly. Ecuador has since been overrun by the drug cartels with murders soaring and property prices plummeting. Wherever we go, we intend to be renters.