Yeah the system feels like it needs some work.
This is how me and my friends did:
1. Person 1 talks to the NPC.
2. Person 2 pickpockets the NPC.
3. Person 2 sends the items to Person 3.
4. Person 1 stops talking and the NPC searches Person 1 and 2.
5. The NPS finds nothing.
6. Person 3 sends the item to Person 1/2.
7. DONE!
Feels a bit like cheating.
I don't think you're supposed to be able to pickpocket everything you want. You being a rogue has NOTHING to do with pickpocketing, everyone can do it. You can avoid getting caught.
You're arguments are rather invalid, since you're basically upset that you cant pickpocket EVERYTHING, but that would be broken.
