I think there are plenty of people who would enjoy the ability to pickpocket NPCs. There should be a limit to how much you can steal in a day. Additionally, you should only be able to pickpocket any given NPC once a day. Some guidelines to prevent this from disrupting the economy: 1. You should not receive more than an average of 0.1 coins per a mark. Since most marks drop junk, this means you could get a decent stack on a lucky grab. 2. Items should be marked "No Value" to prevent getting rich quick. (Possibly a "Stolen" mark should be made and a fence on the airship should buy them at drastically reduced price. This could be added for all stolen goods.) 3. The vast majority of items should be low grade items, those found in furniture, crates and barrels (only these are also no-value.) This makes it more fun when you get something good on the rare occasion, which should be thrown in by the algorithm. 4. The more people you pickpocket in a given NPC city or NPC town, the harder it becomes. 5. If you get caught it is the same as any other stealing: Pay a fine. Fines escalate per how often you've been caught. As of making it more fun: 1. Randomly you should get some half-way decent items, or even good items. 2. The likelihood of getting good items should be based on the difficulty of the mark. The tougher the mark, the better the chance. 3. Players should be able to bolster their chances by having a friend distract the NPC while they sneak around unnoticed. 4. The best item to drop should be a single COTO or worn out low grade ring artifact. These two options would be more of a "success" type thing than actually contributing to the viability of pickpocketing as a path. 5. The Oracle does not approve of pickpockets, even Robin Hood types, and she sees all. All pick-pocketing will decrease your Truth virtue. Pick-pocketing from the poor will decrease your compassion (Beggars, Workers, Monks and Fauns) Pickpocketing NPC enemies will decrease your courage, especially pickpocking fauns. 6. You can pickpocket from humanoid NPCs in adventure areas. The base chance is much lower, but it gives better return as well.