Why do I feel this is a setup?? Still...Alright, I'll be the first to bite.... You're talking emigration, not just 'nomading'--which is that grey area of having a tourist visa but working remotely, thus technically you're not working illegally within that country. Since most countries are very strict about emigration, yes even EU ones, your best bet is to go for that Italian citizenship which if gained will grant you…
> allow access to more countries than any other passport https://en.wikipedia.org/wiki/Henley_Passport_Index differs: looks like an IT passport currently beats a US (albeit not significantly) for visa-free travel.
So yes there is a lot of strength in having an American passport...