First off the bracket tourney looks much more interesting to me than a ladder.
As long as the pilots names are randomly drawn and matched so everyone has an equal chance to draw an easy kill like myself or a tough one like blukitty.
Also, make it best of 5, contest gives you 3 planes, each pilot picks one plane, not to include any plane already chosen by the contest.
IE if contest says p38, p47, and p51d are the 3 planes the pilot could choose the p51b for his plane but not the p51d, as its already been chosen.
If you want to get real fancy, signup web page would also have a poll for your top 3 picks for plane choice. Then on game day you pick the most voted for 3 planes. People would be told what the planes are right before match.