There was interesting discussion about pickpocketing quest being a chore/grindfest in a thread about picking one item up from a stack, so decided to start a separate as I believe this is an interesting topic deserving its own thread. My own 2cc:
While it will probably never happen in ADOM, it could be something that could be implemented in ADOM 2? Active stealth. All races/classes that have stealth skill apparently are all the time slowly sneaking around corners, keeping to the shadows all the time (as much as it hardly ever works no matter skill level). Not to bring other games into this discussion, but in pretty much real life you have to invest into not being seen, you move slower, crouch to have smaller profile etc etc. One should be required to turn sneaking/stealth on in order to have its benefits. And those benefits should also include much higher chance of picking someone's pocket (or stabbing them in the back). Would make assassin/thief gameplay be more sneak up on mob, do your thing, run away to be able to approach second time, speed being main factor.
As a side note, pickpocketing should not be punishable by death by all the villagers/townsfolk, let the sheriff/guards charge you and have some kind of penalty - pay a huge fine, spend a 1k turns in jail. But pickpocketting non-monsters seems like something that should be a thing, that farmer is much more likely to have sold some plants and have change in their pocket than a random troll in a dungeon. With border village there seems like more and more possible victims are there in the game, yet totally not really as the risk is just absurdly high, might as well go for stealing all things from the shop