Not to make this competition too difficult, I see a series of 5 challenges that our two contestants will compete in, resulting in points. Whoever after the 5 challenges has the most points, wins. If tied, there will be a tie-breaker(s) until the tie is broken.
The challenges must be generic challenges that any of us here on Subsonic could compete. No challenge should be geared to favor one contestant over the other, such as naming all the monorail colors and when they put in service. Obviously, we know which brother that would favor....(sorry, Mark86, gotta be fair to Len90)...

To start, I will post the first challenge for our two contestants:
CHALLENGE #1: Both contestants are bound to have many photos from their many trips over years to WDW. And in many of those photos, they have probably taken photos with various Disney characters. So here's what each must do: name as many characters they can they stood next to in a photo. Multiples photos of the same character only counts as one character. Variations of outfits for a character still count as only one character. So, for instance, if you should have 572 pictures of you and Minnie Mouse and Minnie has seventeen different outfits in those photos, it still counts only as one character: Minnie Mouse. There's no need to post the photos, we'll take it on the honor system (however, if a contestant contests the list of the other contestant, then the contesting contestant can audit the photos of the other contestant being contested to verify). SCORING: Each contestant will get a point for each character.
Responses must be posted by Tuesday, June 28, 2011. Late postings will receive ZERO points.
Meanwhile, during that time, that gives us here on Subsonic plenty of time to discuss ideas for Challenge #2, which hopefully we can post after the results are finalized for Challenge #1.