I did not like stealing in BG2/PS:T/IWD at all. Nicking 10gp from someone out of dialogue and only being able to steal proper items in stores did not provide as much fun to me as stealing in, for example, Fallout did.
What I'd love to see would be the ability to use my Stealing skill via conversation options (with the possibility of failure), and, most importantly, to steal from random NPCs out in the world without initiating dialogue. Of course it wouldn't make sense to steal the armor off someones back, but I'd love it if any item that is not currently worn would provide me with the option to go for it. The chance of success could be influenced by the weight or type of the item, and in special cases by how protective the owner feels towards the item.
In the interface that'd show me the contents of his/her backpack and the chance of success, you could fuzz the numbers stronger by how little Dexterity/Perception/Intelligence/Streetsmarts/Awareness the protagonist and the target has. As the last ingredient, add a cooldown to stealing (5 times within 5 minutes or something) much like the gambling/reload cooldown in New Vegas worked, and I would be one happy sonofabitch.
...Okay, this got a little out of hand, I'm not designing the game after all... but do my fellow career rogues think about making Stealing more interesting?