Need a permanent address here in the USA for lots of legal things like health insurance, taxation, and H1B visa things. So that could be solved by borrowing someone's address where there is mutual trust.
Then the next thing you would need is a relatively high speed and stable internet connection because for some reason people think that video chat is the best way to solve problems instead of a simple phone call or slack message or email. That's kind of hard to find in the US for people who are constantly on the move, for both technical and money reasons.
If you manage to solve those two problems, you then have to finance and ensure the safety and security of whatever thing you're living in. And you would have to ask yourself if it is worth living in a van in the woods compared to living in a house in the suburbs.
Good luck!
Probably 20 years ago I did this for 6-9 months. I had a CDPD modem for getting access to the Internet, which was ok for doing e-mail, chat, web browsing (though slowly), and SSH remote access. At some point IIRC I switched to some sort of a hot-spot. My job at the time was managing a number of sysadmins and the projects they were working on. I would also do some amount of sysadmin work, but it was mostly text based.
It was wonderful to be able to spend a week out at a camp site by a river, or out in the woods. My setup was a VW camper van, specifically the Adventurewagen. It was quite comfortable for 4 season camping, but you needed to be economical with water. Power was also an issue, it had 2 "golf cart" batteries, and a tiny solar cell, but no generator. I would often end up running the engine to get power enough to run my equipment, which I didn't like doing for various reasons. YMMV. I rarely had access to plug-in power. Often I would charge up while driving, but it made it hard to park in the wilderness for a week.
Today with better Internet availability, it should be even fewer technical difficulties.
If I were to do it today, I'd probably get one of those "solid state generators" that is just a giant LiPO battery pack. Charge it up using an inverter while driving, or at a plugin. I suspect that cafe's wouldn't love you bringing in a giant battery pack to charge. At the time, in CA, cafes were requiring people plugging in to pay, not sure if that is still the case.