I am not sure that it can be done.
I have done something similar when I was trying to estimate how much side "slop" could be had on a hood latch handle after it was assembled into the rest of the latch a long time ago. What I had to do was mimic the extreme conditions (e.g, handle pushed all the way to the left with the largest hole and the smallest pin, while resting on corner of internal surface of pin)...
I had to do it in sketcher and it was NOT a dynamic sort of thing. Basically, I would have the cross section of each item sketched in, and then pivoted to have it at the worst case condition. You would have to move carefully to make sure that there was no interference. It is all manual. Then do a another one with the items pivoted the other way in the worst case possible condition. It can be done, but it isn't fast or easy, and it can't be done with just mates in assembly because there are too many conditions to satisfy.
I know that there are tools out there that will do this, probably even SolidWorks add-ons. However, I am assuming that you are using plain Solidworks Premium.