I'm too busy to really put the time into submitting a piece for this if it happens anytime soon, but here are some ideas if it helps:
Without there really being a hub where everybody can meet up, I think we will be restricted to two or three categories hosted online -
There could be a "Music" category, where people submit a soundfile (maybe downloadable and via soundcloud) I think there should be freedom for people to operate here to their own taste as restrictions of style and approach will complicate matters for some individuals - perhaps a simpler restriction like max. length of 1.30mins is more feasible. People could submit a short paragraph describing the work which could be serious/pop/comedy whatever...
There could be a "Bent Machines" category, where you submit a youtube demo video which really should be as high quality as possible and recorded well, judging criteria could be originality, sound, quality and/or usability.
A third category if not merged with the one above could be "Paint Jobs" in a pimp my casio style where high res photo's are submitted.
As for judges, I think there should be more than one - either some people are invited to judge the competition for us (I don't have any suggestions sorry) or we just keep it within the forum with the judges obviously not being allowed to submit anything within the categories they host - obviously some credibility would be good
Prizes - well if it's going to be hosted online and there will be no monetary exchange between anyone I think it should go ahead without, I know it sucks a bit but otherwise this topic is going to go around in circles forever unless someone steps forward and donates something!! I think a title should be worthy enough "Bent Pimp of the Year"?
Aid