The hardest part of a switch would have to do with our GM Desk. We currently use the ever moving target of the DMB Universal ID to sort players. Moving to OOTP would involve a different system. Whether or not it's easier, I'm not sure. I'd have to create a new database table (not hard) involving all the data needed from the DMB disk currently (also not hard). I'd then have to create a new column in our player table (also not hard) and update all the other formulae we use in the off-season (not hard, but somewhat time consuming) before going through and making sure the players listed are indeed who we think they are (incredibly time consuming, and sanity checking errors makes me want to rip my hair out).
So, in short, the change is definitely doable if we all decided we wanted/needed to go down that route. The EC wouldn't make this decision quickly, and whomever is in charge of the database at that point would have ample time to make sure all the ducks are in a row before we pushed "Go" on any change of this magnitude.