Wheel changes within a team shouldn't be that problematic, as they can ensure that all the wheels and rotors are spaced identically. It will take a bit more work at the service course, but so be it. This would be further assisted by the adoption of thru-axles for road bikes, which give a more consistent and precise alignment. It's neutral service that would be difficult.
As for cool versus uncool, I don't think the coolness of a road bike has much relationship to the sort of brakes it has. There are definitely road bikes with discs that look dorky as hell (Volagi, I'm looking at you... and hairnet, nothing personal, but that Straggler ain't cool) and I've seen some that look awesome.