While I would love to see something like this happen (and of course have my own writing published :greedy emoticon

, I don't think it would work.
Other sites that have had books published, like Maddox and Tucker Max, are more about a strong personality or net-celebrity (netlebrity?). And College Humor has a stronger editorial presence than RJ, which leads to a better quality of writing.
I think the best shot for a nostalgia site at getting a book would be X-Entertainment. A book by Matt would be awesome.
I've often thought about suggesting that RJ get a dedicated editorial staff. It would lead to articles of better quality, but it would also take away one of the great things about the site- that anyone can have their voice heard.
A middle road option could be having 'featured articles', or 'staff writers', which are subject to greater editorial veto than the regular articles that anyone can submit. (Note that I'm not suggesting that editors or staff writers would be paid. It'd have to be volunteer stuff.)