Yes I think the potential for pickpocketing has high potential for breaking the economy currently. A few things to point out:
1. As of right now the shops replenish each long rest. It would be much better if the resources were finite.
2. The checks involved should be passive perception if behind/active perception if in visual against Sleight of Hand if noticed as well as Stealth
3. It would be neat if after a merchant realizes they have been robbed, they maybe obtain more Guards/NPC for the vicinity.
4. In a tabletop there would be a very rare chance that I can pickpocket Magical Weapons and armor lol. It would make more sense if you can pick pocket things that are smaller in nature ( Potions, Scrolls, Money )
5. Ultimately, I would like merchants to behave more dynamically if it was a tabletop.
Jaz