Except, no, that isn't what I said, at any point. What I said is that pickpocketing as a skill isn't balanced properly. I didn't say I wanted it to be easier. I didn't say I wanted it to be unlimited.
Let me make an analogy. You have combat skills, yes? Unless it is a once per combat skill, you can use those multiple times in combat. They are on timers. Same concept as what I am proposing, except a longer timer.
If you have a conversation with someone and then there is a skill check against persuasion and you win, they don't get a 2nd opportunity to win that skill check... If you roll to hit them and you win the roll to hit them, they don't get a 2nd opportunity to avoid getting hit.
Right now, someone who is pickpocketed automatically gets a 2nd nearly unbeatable opportunity to catch you... unless you apparently shuffle items around your characters based on the metagame knowledge that only the first 2 characters are searched... which no reasonable person would know. I don't know how you figured that out, and commend you for it (I'll use it if the skill isn't adjusted and they don't make it so ALL characters are searched), but there is no reason to think that when they ask to search your party that they wouldn't search everyone.
