The one side flat, one side tapered should make a more stable attachment. However, the contact surfaces are still very small.
I will mention again that the bracket does not move side to side or front to back, it pivots in the channel. You can just pivot it back to the central, flat position.
Woodpecker may have chosen this design as a way to avoid breakage or bending of the Festool rail if there is a major impact at the end of the Woodpecker rail. A 50 inch long rail creates a very powerful lever arm. If the bracket was tightly held in the Festool rail channel, then one of the pieces could be bent or broken if the end of the Woodpecker rail hit something solid while the whole combination was being moved.
By having a pivot point, some of the force of the impact is taken by the pivoting action. Once pivoted, the bracket and rail can flex more easily to absorb the rest of the impact.
If the bracket was flat on the bottom, the inside nut could use the same principle as the locking mechanism on miter bars on table saws. (slit in bar, tapered screw/hole forcing sides of bar to hold against table saw slot). However, that might be a bad idea in the case of a large levering action.
I would rather put up with occasionally having to repivot the bracket than risk bending my Festool rail.