How about the program/game DM selecting a series of locations/scenarios from which to pick? E.g., he could pick the Ravenloft castle in Kale, the caverns beneath Garakesh, a fight scene in Far City, maybe six or seven altogether, and place the fighter in a situation. Kinda like the old Star Trek episode where the crew was plopped down into the middle of the OK corral and Spock had to mind-meld them into thinking it was all a dream.
So the character would be given a situation. The DM would have to design each four of the scenarios to be equivalent, then two to be much tougher, then one mauvais-posterior one (can't say bad-ass in front of Connor). Then, as eight goobers face off, the winners advance in the bracket, a la March Madness! Then the winner gets to play his character in a brand new game designed by the staff - some new scenario - and gets to select a team from the also-rans! That way, his prize would be creating his own team.
Also, and I don't know if this is possible or a good idea, but the rolls in the first bracket could be truncated - i.e., if you roll a 1 or 2, they become a 3, and 20 and 19 become 18, so as to help eliminate the possibility of bad rolls or good rolls determining everything - the skills of the character would count for more. Is that too much manipulation? We may not want a good character blown out because of a bad roll, or do we? Remember, this is coming from the mind of a novice, so bear with me.
Another thought - are we fighting, for instance, Rupert against Nips in a Daven castle? Or Rupert vs. a set of undead from a Daven castle scenario, then Nips vs. some Orc troops in a cave in Kelerak? And does the original player play his character, or does the DM just wind it all up and play everything? Personally, I think the player should play his own character, we shouldn't get it too mechanized.
Question - does each character have to assume his original alignment? What if we go head-to-head and the winners of the first fight are faced off against each other, and they're both good guys? This is only if they fight each other, not if they fight planned bad guys.