This has come up a bunch on the sub so there's decent info out about it, but Clint does Josh's taxes so he does report what he earns with his wnds, YouTube money, etc. He's allowed to make ~$1200 a month without it causing any trouble with his normal SSI payments.
Oprah explanation of it here.
Bite Size (CoSOggy) breaking down his finances.
I am also starting to think about new issues that may come up with a brand new computer that I think could really be hilarious. The biggest one is his passwords. He is obviously the type of person who reuses a password, but I wonder how much he relies on them being saved in the browser? That's what allowed him to still use his debit card even though Clint took it. So unless he has an account with whatever browser he uses, can remember the login to it, and hope it actually synced his info – he could be fucked trying to log into a lot of places.
The laptop possibly allows travel if somewhere has wifi. I wonder if we will ever get a full McDonalds food hack stream live from the restaurant? Possibly not now that he's paranoid of getting kicked out, but there's a chance.