All he had to do was drink in moderation, make his shitty sticks, collect money from weens and he'd be perfectly okay for someone on SSI.
I think I've posted this before in here (or maybe I did in his subreddit), but...yeah.
All considered if he had a decent head on his shoulders he could have a somewhat spartan, but otherwise comfy life. Selling painted sticks and merch (which the fans/trolls would even help him design, if he fucking asked) would pay for basic expenses, him having SSI would help and donations would give him some extra cash to save and/or buy some new toys.
Maybe he could even find some small part-time job somewhere
trolls wouldn't find him.
The problem is he doesn't have a brain, at least not one that functions at least at 50%.
Despite being always broke he mindlessly spends $50-$60 on fast food and God knows how much on booze.
He is unable to keep his accounts (bank and paypal) with a positive balance, every single cent that he has just has to vanish immediately, lest the money start to accumulate dust or something. And then he doesn't keep track of how much he spends and ends up overdrafting, also he never accounts for possible chargebacks on paypal which trolls commonly do.
It frustrates me because I've been a miserable fuck with no luck and a feeling of having no future, I know how nice it would have felt if someone had given me a hand at the time.
But Josh has people trying to help him over and over again and he simply isn't able (literally, his brain just can't do it) to take advantage of the chances he has. He doesn't even aknowledge that people try to help him.
TL;DR: if Cobes wasn't a complete shitshow of a person, he would lead a simple but decent life. But he's a complete retard with very little or nothing in the way of redeeming qualities.