The funniest part is where he says he wants to cut down his list because the hats cost $30 a piece. If he wants to choose a hat, that's fine--that's the image kids get of how these things are done--but I can't help but think that behind this "tradition," like so many others (think weddings for a quick example), is somebody who wanted to sell something (in this case, some hats).
If I were him I'd just get the hat of the school I wanted to commit to, put it in a box, and wrap it with a nice bow on top. Then I'd unwrap it in front of the crowd and don it proudly. Cost = hat + wrapping paper + bow. Much more financially reasonable.