In both of my drafts, Carlos Guillen and Orlando Cabrera dropped to rounds 9 and 10, respectively. However, every shortstop taken before them were taken in the first six rounds (Tejada, Jeter, Rollins, Furcal, Nomar, Renteria, and Young).
So my drafts weren't quite as crazy as yours, but I think there are significant tiers after Tejada and again after Young (assuming that's the order of the other 6 guys). Then another one between O-Cab/Guillen and Figgins, Matsui, Crosby and Uribe.
They're basically going as a group, like the top tier of closers vs. the bottom tier. If you have faith in O-Cab and Guillen, then hold off. If not, just hope you aren't picking on the wrong end of a run!