Questions about pick pocketing

[Kaylon]

I haven't tested too much, but what are your experiences with pick pocketing?

1. Have you found npcs hard/impossible to pick pocket?

2. Does the party contribute to your skill checks (for stealth/sleazy hand)?

3. Has Sleazy hand any effect on pick pocketing? (from my experience all it matters is to be undetected when you attempt to pick pocket) 

4. It's worth having a specialist for that (maybe hire an adventurer and spec him just in stealth/sleazy hand)?

5. Is there a cap to the assist bonus?

[Manacore]

1) Yes at the beginning of my run, not after a few points spent in the skill

2) I don't know I've dedicated 1 character to this with stealth/sleazy hand

3) I think you can't steal some items if its not high enough but it's rapidly not a problem with 5 or 6 points invested

4) I do have a specialist for this, It makes some quests easier but it can mess up some dialogues if you steal the npc before talking to him

5) dont know