I was thinking about what Chris will do if he can get his tugboat back and get into a somewhat stable living situation. I think his toys and games will be the number one priority above housing and bills and he will absolutely have to get all the stuff he missed. How much will he blow right out of jail?
Assuming his game consoles were not thrown out, he'll need the $30 MLP game that came out last month. Internet costs around $50, and he'll need a $10 Netflix subscription to watch the new Sonic show with tan arms. If he gets the Sonic movies on DVD that's another $28.
He's going to spend a lot on Legos: going by Amazon prices, a $34 MLP set, plus multiple Mario sets, I'll estimate the Mario ones at a total of $200. There's a fantastic Optimus Prime set that Chris just won't be able to live without, it's $170. The Sonic set is $70, but he's going to need more Sonic minifigures. They're sold loose on eBay for $20 each, so I'll assume he orders four more of them that he can modify into his characters with Crayola Fuckin' Model Magic and the deluxe multicolor package of that is $16. I'm thinking five figures to make the Chaotic Combo.
If he gets back into selling art, he'll need supplies. He uses the cheapest stuff available though, so I'll say $20 to get started for printer paper, markers, and pens. Keep in mind that that's almost like work for Chris so it might be low priority.
Grand total is $708. If there's a delay in getting his tugboat reinstated he'll be begging for donations the day he gets internet access.