I don't have any experience with the Trek Pilot, but from what I read it is supposed to be a bit more upright, with a little more relaxed geometry.
The biggest problem is that is takes some time to get used to go from riding a hybrid to a road bike, so whichever bike you pick will feel a little strange at first.
I think you will have to try as many as possible. I don't think you'll need to start with the top of the line Pilot. Again, if you have good feelings about a particular shop, see what they advise.