My wife came up with that idea, as well. It could work, except for the big tangled mass of copyright. As far as I know, Brad has never claimed copyright on anything except the site's code. We could assume this means he owns all the stored comic code, too. Fair enough. But what about the art? All the stuff that I have drawn and submitted for use with this site is mine - I own it, and Brad (along with everyone who uses this site) is allowed to use them. If Brad wanted to make a book, I would not hesitate to give him permission to use my images (though if it sold a million copies, I may be a bit miffed *grin*).
...but what about Penny Arcade? Goats? explodingdog? These guys gave permission for their art to be used on a free website, not in a book, which is not free to all. What if one or more of the owners of this art said "Sure, use my art, but I want a share of the profit." Suddenly, Brad is in royalty hell, keeping track of percentages and margins. Yecchh...
Brad's own clipart characters might be a problem too. If Brad got the book printed, then got a nasty letter from some guy claiming that he drew the Asian girls, and they are not public domain... Yecchh (again)...
Of course, all this may not be a problem - everyone who has given Brad permission to use their art may give the thumbs up. Failing that, we could select only strips that use art with "permission to print", or even get all the regulars to write (or even rewrite) a whole book's worth of strips which only use the permissable artwork. (That last one was my wife's idea.)
...would it sell, though? That's the main question. Plan 9 or someone similar might print it, but if hardly any copies sell, there isn't much point, is there?
I must be honest - I think a big, prominent guilt-trip nag banner at the top and/or bottom of every page on the site would be the most cost effective, just something to remind users that, if they are enjoying the site and can afford to send a few bucks, the administrator would really appreciate it. *shrug*
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