[sebastiangraef]

For sure. I've been living a nomadic life for three years now, not randomized because I prefer picking my locations myself but I could do that. Good passport, so this problem doesn't apply to me. But I've also met plenty enough Indian or Filipino nomads in Asia. If you got the remote income stream then you can solve the visa problems.

[dorchadas]

I'd love to do this for a while, but getting that remote income stream is the issue for me, especially with student loans to pay off. Any advice?

[sebastiangraef]

I basically quit my job without income and got freelance clients after traveling for a while. That might be not everyone's cup of tea so probably better to get that sorted before leaving. There are quite a lot of fully remote jobs now but tons of competition and mostly "US only". Freelancing is probably the fastest way to get remote income. Best is to have some kind of retainer deal for x/month in my opinion, instead of always hunting new projects. SaaS or any kind of online business is more of a long term play.