running 14-2 romex
Not wanting to get into the details of the code, or to get into the interpretation of 334.80, that is what I meant about it being a contentious issue.
A) As long as you stay under nine CCC's (current carrying conductors) there is NO issue with derating #14, #12, or #10. Ten or more CCC's derating becomes an issue.
Four 14/2's is eight CCC's.
B) Aside from the fire stop issue, not all AHJs consider running cables loosely through bored holes "bundling". In fact I see more that do not than do.
Sometimes I feel like if I answer any more questions it is like someone trying to climb over a fence to jump off a bridge and me giving them a boost.