It's been a while.
Currently, theft via pickpocketing is pretty all right. When you're not targeting specific items, it can still be a fairly lucrative endeavor. But, to be lucrative, it requires you to do it all the time. After a while, this starts to feel exploitative in that you're just targeting people when they're vulnerable and moving on, over and over. There's virtually no incentive to target bigger fish because you're not going to get anything different and, even if you do, there's a limit to how much you can get. The driving mantra, then, is quantity over quality. I think everyone will agree that it's super boring and tedious to have a thief running around trying to rob the same people ten times per day.
So, the problem then is the lack of targetability. With the ability to target high-value items in people's inventory, the focus shifts from quantity (rob everyone) to quality (rob the rich). The current targeted pickpocket system is horrible. It lacks fundamental mechanics to make the interaction fair, predictable, preventable, or interesting for anyone involved. When it succeeds, it's a miracle and the target is pissed because there's not much they could've done to avoid it. When it fails, it's expected and there's nothing the thief could've done to make it succeed.
To be successful, a good theft system needs three things: fairness, predictability, and preventability. Here's an attempt at creating that.
Pickpocket (not targeting an item)
Pickpocket (targeting an item)
Change the base success percentage to 1%, which I suspect is lower than the current success percent.
Case (new skill)
Syntax: CASE <target>
Balance: 2 seconds
Case your target, watching how they react to your presence and, more importantly, how they choose to safeguard their possessions.
When you case a target, you (roughly) double the percentage chance of pickpocketing a specific item. After one case, the chance is 2%. After two cases, it's 5%. After three cases, 10%. After seven, it's 85% and that's the maximum. Cases last for one real life day: at the serenade, they all automatically reset.
Targets receive a message for every case used against them. The first two cases have messages to the target. The next three have messages to the room. The next two might do something unique, like forcing the character to yell that they're being cased.
This system is fair in that it allows the target to avoid the thief: after they see the first case, they have 14 full seconds to avoid being fully cased. It is predictable in that it allows the thief to prepare for and depend upon the performance of their skills, while still having some element of randomness involved. It is preventable in that it it still relies on bypassing selfishness, rewear triggers, and so forth; moreso, it is preventable because the target is notified well in advance about what is happening.
Anyway, there's an idea.