If you want to foot my 10 dollar entry fee, then I am all for it. However, I think it is evident that adding the money element would prevent a lot of people from signing up in the first place, which hampers the excellent growth of this community, and it also can be a deterant for good sportsmanship, a la win at all costs.
It is great though to kick around new ideas. The league is great as is, but there is no reason it couldn't get even better.