This has nothing to do with oversizing the raceway but rather how many holes can you drill in to a NEMA enclosure (say a NEMA 4 for example). NEC is silent about this (i'm pretty sure).
While I could drill as many holes as could fit into one side of the enclosure, too many and the enclosure will loose it's structural integrity and the side with all of the holes would start to bend.
I also don't believe the limiting factor is the number of conductors one can fit in a box either. Imagine if I were able to put up to 100 conductors in a box (as determined by NEC) and bring them all in using multiple conduits, or cables in my case. I'd be smart to bring them in on all 4 sides of the box, but if other obstructions to entry limit me from using the other 3 sides, I may elect to penetrate the bottom of the enclosure. At some point I'm going to have to use a box with a larger surface area on the 1 side.
I'm pretty sure I read somewhere where there was a limit.