I'm trying to keep the same orientation of faces of 5 extrudes so that they allways "point" in the same direction.

The problem is in the main assembly the individual parts will not rotate AND translate to properly solve the problem.

When you open up the assembly The idea is that the center extrude should translate so that the last two mates are coincident and parallel to the plane. This should be solvable even with all the sub-assembly mates used to keep the faces parallel. It does require that each individual part rotate like it does when you edit the sub assembly which maybe the reason why it breaks? Possibly SW's isn't taking into account the individual part rotation's to solve the mate?

Are there any ways to solve this problem simply? I want to avoid having to apply a mate between each part and the plane.