How high up in the seeds would you be planning to go with the "all-upset" picks? I could certainly see picking a bunch of 9s,10s,11s, and 12s - but if you start picking 13s and 14s on that math, you're knocking out 3's and 4's who would be expected to win more than one game.
To me, in a pool like that, it would make sense to always pick the upset in the first round if you think the favorite would lose in the 2nd round regardless.