I've been to Lolla the last three years, and I've never been able to use data while at the festival. I have no doubt that the results of this contest will be cool, but unless they bus in extra cell antennas, I doubt I'll get anything out of this.
iPhone on AT&T? At SXSW, I read they do add some extra cells for that period. I wonder how they make a decision to do that? If you can't tweet they don't get bad press about poor coverage.
Cool idea. I think I'll try it. Although, honestly, the prizes might be kinda lame. :) How about 10 tickets.. or a cabana instead :) haha.