One thing we discussed 'bout pickpocketing that I thought would be important was having the thought bubble pop up when you're close, like kinstone fusion in minish cap. So that way there wouldn't be "hey pickpocket me" bubbles floating around all over the screen cluttering it up. Also I think it'd feel more natural, to have to get close to someone to scope them out and see if you can get them.
The other discussion we had was about having talk and pickpocket on different buttons (spacebar for talk, the contextual action button for pickpocket). The situation in questions was "I want to talk to someone but not pickpocket them", slash also I don't like the idea of having to walk around an NPC to get to their "talking side". We've always been able to approach an NPC from any side and talk. Pickpocketing makes sense to just do from behind, but talking from only the front, or only front or side doesn't sound that great.
Another thing to bring up, this might as well be the place, NPCs that stand in one place and pivot to face different directions randomly are lame. Especially for pickpocketing. I know it'd be more work to have all the NPCs in town have their own routes they follow, like Majora's Mask, but I think it's worth it. It could be simple, like they just walk in a circle around a fountain or go down the street and back, but I don't like the dudes who just pivot randomly. It made pickpocketing harder in a not-fun way in the demo.
Also, something we never discussed is how the rewards for pickpocketing would be decided. Is it going to be each individual who can be robbed has a prize? Or would it be more random? Presumably you can pickpocket the same people multiple times, perhaps after you leave the area and come back. Anyway, what I thought might be fun is occasionally when you pickpocket someone instead of rupees or a heart or whatever you might get, you get a message that says "you deftly swipe a handful of... lint?" Or "all that was in his pocket was gum. And it's already been chewed?" We could easily come up with like a dozen or two funny messages to put in there sometimes.