Although I've played guitar for roughly 13 years, I've never tinkered with the truss rod. I'm guess that this is needed to fix my current problem:

Problem: I've been examining the neck to no end. I honestly can't notice any bending/warping; I'm not sure what else to look for. Anyways, if I bend on the high e-string, the sound will cut out. However, I can bend on the 14th & 16th fret with no issues. Moreover, I can bend all the other strings on the 15th with no problem. It all resides with the high e-string and the 15th fret.

Any ideas?

Well the action maybe to low but from your years of playing i dont think thats it. one of your frets may have been knocked off level and causes the e string to catch. or theres a gash on a fret that catches.
How is the fret when you don't bend. Is the sound full or does it sound muted. Do you need to press that fret extra hard to make the note ring.
does the sound cut out totally, or does it just lower the volume substancially?

if it buzzes slighty afterwards, it might have a notch or crevis in the fret that catches and mutes the string

Epiphone Hummingbird
Epiphone Futura Custom Prophecy (Twin EMG)
Vox Valvetronix VT20+
Vox Wah
Boss MD-2
Danelectro Cool Cat Drive
Boss EQ

I have this exact same issue with my 10th fret, it plays fine but for bending up, the sound gets muted or is barely audible
Takamine EG341SC
Godin Freeway Classic -> Boss TU-2 -> Fulltone OCD -> MXR M173 -> Boss RC-20XL -> Traynor YCV50 Blue