I was not one of the 20 Smackdown participants but joined later. Found that I had fun but “ran out of gas” (as many do in active investing). I like your idea for 2008. Since there would be multiple winners (e.g. anyone on the highest point of the efficient frontier), I would suggest some tie breaking rules:
(1) Who is the laziest – that is weight the winners by number of index choices. If someone has only one index and have the highest return for the lowest risk with the least expense – they win.
(2) Limit the number of trades. Since timing is a no-no in index investing – he who has the least trades wins! Or maybe even the game limits the number of rebalancing to 3-4 times.

Keep those great shows coming