Picking apart Skyrim's pickpocketing

I was recently the willful accomplice victim of a successful plot to pull me back into Skyrim. I put hundreds of hours into the game back in high school but had mostly escaped — until my friend texted me when I was sick. While playing through it seemed like the pickpocketing chance was bugged. Follow me down the spiraling rabbit hole to reverse engineer what backs it, what causes the bug, and just how much gold I can get away with stealing.