However, I didn't read all the posts, so if no one brought this up yet, it may be considered gambling and could be illegal. Usually there is an exception if the money goes to a charitable cause. I can look into it if you guys want. But it could get sticky because the proposal crosses state lines (internet), therefore it would be subject to federal law (interstate commerce).
*edit - just went back and skimmed through. It looks like CMC is on the right track by considering the legality of this.
**further edit - make sure your atty consults not only Illinois law but federal law on this issue.