His favorite thing is the hat, "because it really embodies the totally random outcome of these contest".
I think it shows what's wrong with his idea: he has a prize that doesn't really have any significance to him. However I'm guessing other entrants to the contest (if there were any) actually are fans of the show, and would value the hat much higher.
The hat came with a Visa gift card. If you look at his full text list, it's actually pretty impressive and full of things that would probably have significance to him.
I think it shows what's wrong with his idea: he has a prize that doesn't really have any significance to him. However I'm guessing other entrants to the contest (if there were any) actually are fans of the show, and would value the hat much higher.