Clarified question (tl;dr)
After reading and profiling with all the results covered below, the problem seems to boil down to the GC not collecting G
After much research, reading, and profiling I have been able to prove that our IIS memory usage is actually within the standard; this was done using the SysInternals Test Limit utility to push the server's physical memory usage to near max, once this was done all of our applications released their memory.
We do still have some kind of memory issue in our test environment that I need to investigate but at this point I think I can confidently say that this is entirely unrelated.
Moral of the story is to not assume that the cause reported with the issue is correct.