I actually know someone who did this.
'Course I grew up in Alaska, which is a popular choice for drop out candidates. I grew up in the southeastern part of the state (where the weather is less harsh and therefore it’s more feasible to drop out and go build yourself a shack on public land somewhere and go about your business).
The guy I’m thinking of did precisely that some 25 - 30 years ago. Dropped out, moved to Alaska with a modest amount of hard cash (I think it was 5,000), and built himself a little place out on public land. Everyone calls him “Hippie Chris”. This is because nobody knows his actual legal name. For many years he came into town twice a year. Those trips he generally sold/traded some goods (furs, actually, and some handcrafted things, as well as surplus produce and fish/game) and used the proceeds to buy things he couldn’t really make himself. He also occasionally worked here and there as an odd-jobs guy for strictly cash-for-labor. He was never in town for more than a couple of weeks in any given year, and some years he didn’t show up at all.
He was a popular hire when he was in town, though, because the man is an absolute mechanical genuis. He can fix any damn thing at all.
For the last 5 years or so, he’s been making more frequent trips into town (and hiring himself out more often, still cash-for-labor though) and last winter he housesat for my parents (they spend the winter in Arizona these days) instead of spending the winter out at his place.
He’s essentially still dropped out though - just being more social about it these days. Still no job, no real ties, no rent, no responsibilities.
A few years ago, the federal government actually opened up homesteading (as in Old West homesteading - live X years on totally unimproved land and you own it at the end) on some of the federal land near my hometown, so my hometown has a higher-than-average percentage of drop-out mentality folks. A lot of them now proud land-owners, courtesy of the federal government. A few of those were so freaked out by the responsibility of land ownership that they promptly sold their places when they were granted title and went back to being dropped out.
Mostly the town views Hippie Chris and the other folks as slightly weird, but decent folks. It always struck me as a lonely and hard way to live, but I know people who find it fulfilling. YMMV.