Let's see.
Initial questions: Motivation, Money, Social Interaction.
None of the above is a given with our pet lolcow.
Motivation: Chris doesn't want a job, indeed, the greatest single failing of Chris is that he doesn't really want ANYTHING enough to fight for it. So where's the motivation to apply to college, go through the admissions process, and even pursue a dream?
Money: Chris' monthly tugboat might be free money, but its also not very much free money. 4 Year colleges are expensive, and Chris isn't going to work, nor make cuts to his lifestyle.
Social Interaction: All people on the internet are trolls, all men are jerks and all women have an infinite boyfriend factor. He's got to go to classes, work with others on group projects, make presentations and meet basic social standards. He's in serious trouble here even in the short run; he'd be crashing and burning within the first month.
All told, CWC would need a massive lifestyle change to give this a shot. With no transfer credit from PVCC, he'd have to go through at least a years worth of Breadth classes. This includes things like calculus, fairly advanced writing and social sciences. Most people I know can't easily do these things--they have to fight hard for them. Chris has never fought for months on anything; even things where he supposedly put up a fight against Trolldom came with a silent prodding to get results. There's no prodding in college; you can sleep through your classes and skip homework at will.
I give Chris one month, tops. He won't run out of money immediately, but he'll run out of motivation and quite possibly die on a group project. It's over, and its over quickly.