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There is no doubt this is a staggering problem given the unpredictability of college basketball. I basically keep circling back around to the same conclusion as I try to design these scenarios, you need to make aggressive predictions and accept that the whole pool cannot cover everything.
It is going to come down to having a really good way of predicting particular matchups. Unfortunately I think that is an impossible problem, it is hard to matchup two teams and predict a winner with even 70% confidence. If you could you would see a lot of large point spread predictions since to predict at that level you have to assume that one team is just going to pull away over the course of the 40 minutes.
The best we can do is target where to invest those matchup decisions as accurately as possible. To really make this happen you need a lot of pre-bracket scouting of the teams during the year so you gather a good analysis of their strengths and weaknesses. You need to predict as well as you can how a team can matchup with any other team you have scouted.
If you can pick a favorite to reach the championship game, and can restrict the Final Four to about 2 contenders per region, you can chop a lot of possibilities from the top of the tree. So after the region analysis post I will probably take a tangent off into game prediction, even though that is my weakest area it is of course the most important.
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