He could get into legal trouble again and if he had access to money, he would likely pay for another expensive lawyer like Rob Bell to make it go away. He cost enough to burn through whatever inheritance Bob had left his family. Chris said this amount was in the tens of thousands of dollars.
Chris and Barb drive crappy cars out of necessity, I think. Chris would probably like a nicer, more reliable one, which he would ruin somehow, either through lack of maintenance, getting into accidents, or with bizarre Sonichu-related customizations. And he'd probably buy one for Barb too. He has bought her expensive gifts before like the $400 gold necklace.
Regarding video games, with enough money Chris would likely buy every video game he could find. He would buy games and leave them sealed on his shelves. And he'd buy a lot of Lego sets too, and they'd be the big ones. Those can be several hundreds of dollars each, and you just know he'd buy a whole pile of
the Sonic kits.