I've just spent the past 10 minutes casting Guidance on my rogue to pickpocket a trader, steal some things, and run away, waiting for the trader to exit their "A pickpocket?!" phase where they walk two steps and look for evidence. Once they go back to their regular state, it's right back to pickpocketing.
There should definitely be more consequences here. Sure, if you fail the pickpocket, you have to answer for yourself by either bribing, persuading or murdering, but even on a successful pickpocket, traders should take more drastic action ESPECIALLY if they've been robbed for the sixth time in a span of 10 minutes. Lol.
Possible consequence: trader unavailable until after your next long rest. Effectively shutting down their shop as they're investigating and avoidng further robbings. This would only really be meaningful if long rests had more consequence themselves. So, it's not a perfect solution by itself.
Another additional consequence could be that if you've pickpocketed a trader more than once, the target for the Sleight of Hand check on all items increases for a while. Essentially a sign of the trader putting more security in place.
I'm all for rewarding players for successful robbings, so long as there are systems in place that prevent them from exploiting.
Just my two cents, though! What do you folks think?
