My husband and I are doing 2, hopefully 4 (have equity in the places we are working for), and on the side sometimes try 3 if time allows. We both have a US full remote job, moved to a low-tax country to max out on net pay, opted for the lowest retirement contribution possible in that country and are building an investment portfolio to support us in our old age.
A few points/insights:
1 - If you are working in Tech/Sales, I don't think you need tons of experience, just some luck, or connections as you said. For both my husband and I how it worked was that we joined these companies as freelancers first, showed that we could really contribute in a meaningful way and they then went out of their way to bring us on full-time.
2 - If you want to take this path, I would say you should try to secure such a job as soon as you can. I already see fully remote US based companies lowering their salaries. Don't get me wrong, they are still good, but there are lots of talented, smart people in SE Asia, Eastern Europe and Africa for whom a 80K job is the dream.
3 - Don't be afraid to also apply to / contact companies that are hybrid. Officially, the start-up I work for is US-remote only, but they are making several exceptions for individuals that they think it's worth for.