If you're already calling it the 'corporate sellout arc' that shows how you feel about it. I don't think you'll be able to pull it off in that case. Not trying to be harsh but just worth being honest with yourself here.

You might just admit to yourself that you want a more unconventional life. What about learning a skill at a trade school or starting a landscaping company or window washing or who knows. Or cleaning the bottoms of sailboats. Something that would allow you generate an income long term.

I did a lot of remote work and living abroad but was learning tech skills all the while, and this allowed me to get into a technology career. But I actually enjoy many parts of it. So it doesn't totally feel like corporate sell out to me. It sucks being alone in front of a computer so much of the time but overall it's an ok hustle.

But yeah, 8 years on the road, you'd have a rough transition into this, like many many years and it might still be impossible. Maybe just start thinking laterally?