Look at the video clip in post #74. Yes, he wants to win. He seems to know exactly what he is doing being on the show.
Yes, he would benefit more by winning, fame/$ wise. Happiness wise--that's another question.
Is David Cook better off from winning? Yes, he compared it to his pre idol album and how hard that was to sell.
Is David Cook happy? I don't know, but the cloying fans are getting to him--he posted a "back off" message on his site.
Apparently one or more fans attached a GPS tracker to his bus; they try to call or get to his hotel room, etc. (And how does this differ from other popular rock groups that have cloying fans? Don't know.).
Looking at Melinda doing a "spring break" tour with other former idols...it's probably better to win; spend the time with the cloying fans; put the $$ away and in a few years do what you want.