Desperate Challenge
Hey Cal- You're right, desperate students is probably the key anchor to attract attention. They will also buzz to their friends about the post. However, I think its more provocative to include the creepy adult.
I think it would be cool to pit the creepy adult against the college kid against the homeless man, etc. As a social experiment it would be interesting to tally results and see how, when, and for what reaons people give. Perhaps there would be a entry space for donors to explain why and how they may their choice.
I think the snobby college kid could get a run for his money from from the depressing, fourty year old virgin. This type of competition may drive repeat donors who suddenly have a stake for their choice to win. Could we include a forum for the participants to talk trash or just communicate with each other? As cal stated, each desperate participant needs a goal to hit as well, at which point they are no longer deemed desperate.
As for the revenue model, I'll push the typical ad/sponsor model and say... I'd like to put the participants up for coporate sponsorship and we take a cut. It forces corporations to make a choice and state their side... which is lofty, but interesting. (IE Kaplan sponsors a widow that always wanted a degree over the college kid that wants a cancun trip)