What if Bards and busking could be an alternative to accessing the same loot tables as Pickpocketing but in a non-illegal way as an alternative for people who don't want to be a criminal.

Suppose there's a Bard Skill Line where each passive skill unlocks a different type of minigame to reflect a type of performance (e.g., playing an instrument, performing a trick). You unlock what type of minigame/performance you want your Bard to do.
The more you invest in the skill line, the more intricate your performance can be (but with a longer and hence harder minigame). How well you do the minigame translates into a score.

During your performance, the game records the NPCs in range (who attended your performance?), and whether there was an overlapping performance that was complementary (partner?) or competitive (rival). Partners improve your performance slightly (duet? troupe? band?). Rivals improve each other's performance more IF you are both score approximately the same (interesting grudge match!) but reduce both if the difference in your scores are too different (distraction).

A separate passive locked by both skill and achievements might let you have Groupies/Fans, a guaranteed friendly audience to increase your score.

Based on the final calculation you get some loot -- mostly a few coins, but sometimes something interesting, just like Pickpocketing.
If a crowd is overworked, they'll give less loot or no loot because they've already given that loot away. And their loot availability is shared with any pickpocketing attempts that may have happened already.