I was wondering if pickpocketing in IWD2 scored something as massive as the free action rings from 1. I noticed that it tends to reward money now, but in multiplayer that small buck doesn't repay for the many reloads.

Even potions or small stuff to sell would be too mundane, are we talking about some big shot to be stolen?

In IWD2 pickpocketing requires more reloads and is less beneficial than in IWD1.

In Targos you can pickpocket some items which are nice at the beginning, but you'll be able to loot or buy better stuff later in the game.

Lord Ulbrec and his wife have a nice item each and one of the customers in Deidre's weapon shop has an item which grants +1 to all saves in normal mode (The HoF version is great until the end however).
You can also pickpocket many things from a priest in the hospital tent, but it's extremely difficult.
You also get an extra beneficial dialogue option if the character who talks to the ill seer in this tent has at least one pickpocket skill.

Overall I don't think pickpocketing is worth the time and resources you have to spend for it in a normal mode game. You won't regret just ignoring it.
If you powergame HoF mode you might want to pickpocket once to get this special item (1 skill rank in pickpocketing can be enough to succeed) and nothing else.

Got it! I wonder why they made it so unfriendly. Was so fun to steal everything in Morrowind.

I wish it was something that they'd paid more attention to as well. That's often a big part of the fun of playing a thief. I wouldn't want it to end up netting you some uber powerful stuff every time, but it would be cool if you get get the odd good item, and some minor stuff that's actually useful as well.

I'd also like it if instead of everyone turning hostile and attacking you so you've pretty much no choice but to kill them, if there were different responses. Maybe some go hostile. Maybe others get angry and demand their item back or they'll call the guards. Maybe some say keep the item, but later on there's a situation where they hold it over your head as a blackmail threat, maybe some of them demand the item and payment or they call the guards. Maybe some just call the guards outright. Or maybe some of them will let you bluff your way out of it ("No, no,it wasn't me. Must have been that guy that just left"). Maybe you can intimidate your way out of it ("Call the guards and I'll slit your throat. Say anything about this and you're dead.")

When they call the guards, you're thrown in jail and have to either buy your way out with money or your best item (if you don't have enough money) as your fine for robbery, maybe you can bribe a guard to let you out, or you can escape if you have have a Rogue in your party with high enough skills. Or maybe a short trial scene where you can accept a fine, a small quest of atonement from the towns administrator or local temple, or you could even argue your way out for little or no penalty.

I realize all this would have been tons of extra work for the devs, but it would be so much more fun and really lessen the temptation to reload if the pick pocket attempt fails.

Hardly anyone would benefit from this since 99 percent just reload their savegame when they get a minor penalty.

You could say that about companions dying as well, yet that's part of the game. In fact, that was a big complaint about Dragon Age (the companions don't die, they just fall unconscious until the battle is over). There are tons of other things people with reload to avoid or change. Just because some people will reload to avoid something is no reason to not have it in the game.

Me too, preferably with a set of brass knuckles in a sound-proof room and with him tied to a chair.