I was wondering if anybody knew about any worthwhile items that could be pickpocketed in IWD2.
I already know about the Lucky Knucky/Young Ned's Knucky that can be pickpocketed from Jemeliah in the Gallaway Tradepost in Targos, but I don't know about any others.

Ulbrec - Ring of Protection +1
That wizard lady - magical scrolls
Oswald - Potion of free action IIRC

The monk leader (the one that leaves the monastery IIRC) has a Ring of Charm. It gives +2 CHA to the wielder.

Scroll down and learn (http://www.sorcerers.net/ubb/ultimatebb.php/topic/14/2035.html) ;)

Yes, but there are only two items mentioned. I was wondering if there was more.

Ulbrec - Ring of Protection +1
That wizard lady - magical scrolls
Oswald - Potion of free action IIRC I've also gotten oil of fiery burning and potion of explosions by pickpocketing Oswald. BTW, if you tell him he owes you five gold (when you first initiate conversation), he'll give you the free action potion.

Picking Guthewulfe's (the trader at the Salty Dog)pockets will get you his wolf charm and a bottle of braehg, and you can swipe a luck potion from Kickshaw (one of the Iron Collar mercs).

Picking Guthewulfe's (the trader at the Salty Dog)pockets will get you his wolf charm...Acutally, if you've got a strong enough CON (I think like 16 or more) you're better off playing his drinking game because not only do you get it, but you get experience from it as well.

Umm... you guys all missed the Lucky Knucky +1 Luck and Saing throws, from the guy in Bottom-right of the Gallaway Trade House

Don't forget the temple of helm.
The diviner has some misc stuff and you can steal cleric scrolls from the clerics but I almost always failed.

That brings me to my question. I have a Fighter 4\Rogue 2 currently and have dumped all possible points during leveling into Pickpocket. I forget how many points she has right now, but I have been successful in pickpocketing everyone in Targos with the exception of the two healers in the temple in town. How many points do you need to be able to pickpocket them?? I know when I've played in the past that the only person I had trouble with was Oswald. But for some reason, that doesn't seem to be the case this time around. When I was picking Oswald, I only failed once or twice. Also, and this is truely an annoyance, why is it that the majority of the time a pick fails is when the target has nothing left to steal?? I would think that if they have nothing left to steal than it would be an easy check.

Uhm, cause someones hand that far down my pocket would be more noticable?

I don't know the pickpocket dc's for the game. Never was a fan of pickpocket for rp reasons.
Try doing it with you rogue just before you go off with oswald and see if it's easier. Or try a search on the forums and see if it's been discussed before.

"Did you touch my butt?"
"Sir, from where I'm standing that's physically impossible."
"I know your tricks."

Yeah, I'm pretty sure they'd notice you sticking your hand deep into their pocket. Especially if you're reaching in to grab their wallet.