[Brak]

I have noticed the same thing, the results from a pickpocket attempt do NOT seem to be anything other than a series of scripted events based on your pickpocket skill. I have even tried cheating, by saving and reloading, but the results are always the same. It does not seem like it is a "die roll" at the time you attempt the pickpocket but rather the dice are rolled prior to you initiating conversation with the person. And the dice for every subsequent attemp have already been rolled as well. Example...I try to pickpocket the rapax. First attempt fails without the rapax noticing, second attempt also fails without him noticing, third attempt fails and he gets upset. So I reload my quick save from right before I talked to him. And the results are the exact same. 4 reloads later with the same 3 results, I have decided that the development team was smart enough to not allow this kind of cheating by pre-rolling the chance that pickpocket attempts will succeed/fail before you even try it. So the only way to practice is to try to pickpocet everyone you see. When you succeed leave the screen and save. Then try again, if you fail then it's time to reload and move on to someone else to practice on.