Josh could survive for quite a long time, I'd be more curious about a homeless saga, the human body can take wild amounts of punishments. If you're curious look around at your local homeless population, 40's, 50's 60's, often polyaddicts who've abused themselves as hard or harder then josh, the duster is easily the most dangerous thing he's doing though. He could drop dead at any moment, but I wouldn't be surprised if he made it into his 50's or 60's, at least a 50/50 chance.
I'd be very interested to see how he reacted if he got evicted again, likely the only thing to push him to do anything different, Josh is soft and doesn't have any experience sleeping rough or having to interact with other mentally ill degens that is the shelter system, which I assume is well beyond capacity if it's anything like most other small to medium size cities right now. I'm sure Clint would bail him out at least once or twice more to save himself the long term headache and too keep josh away from the do-over family, but he absolutely isn't going to let Cobes live with him again, and rightfully so. But if he ended up homeless Josh would implode, but given he's technologically retarded, it would likely result in an even worse content drought, but I am curious, beside broadcasting his downfall and having paypigs he isn't that wildly different from tens of thousands of other people who end up homeless every year. I do feel like it's only a matter of time until he does something dumb enough to get evicted again.
His teeth are weird as fuck to me to, they've hung on better then your average meth head, look at gothie, bitch had her front chompers gone earlier then josh. My only guess is that they actually had some dental intervention and had that shit pulled when it was clear they were beyond repair or caused enough pain, and josh is just sexy gothic rockstaring his way through the pain and obvious need to go to a dentist and face the muisc.
I guess this is why Josh is so facinating, he really is an engima of retardation, but he is basically a documentary on how your average panhandler ends up on that street corner, albiet with more comedy and a better support system.