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Sounds like fun. Rather than just bragging rights for doing well, how about putting some stakes on this?
Like...top 4 finishers get the rest of the group to make a donation to a special cause. (Put a cap of $20 on it.)

At the end of the season, those that don’t finish in the top 4 donate to the cause of one of those 4 top finishes.
i.e. I could designate that should I place in the top 4, I want the others to contribute to Soldiers’ Angels. You could designate you want the money to go to Free Republic.

Those that don’t place in top 4 could choose which cause they want to contribute to among their 4 choices.

This way, there is a true incentive to win besides bragging rights. And since we are an honorable bunch here, I would assume everyone would honor their commitment.

I have done this before, and its really fun.