I have just found a bug with the Pickpocket career. When you switch an item with another, you get a dialogue box pop up asking if you would like to retain the ability of the old piece of gear but you only have the options 'OK' and 'Cancel'. Whichever one you choose, nothing actually happens (no switch of ability) and the dialogue box continues to pop up on each new page you turn to.
Furthermore, there were two occasions after I picked this career when I selected an item reward, equipped it (it showed up in inventory) and then when I reach my next fight, the item switches back to whatever it replaced and then you are stuck with the old item (Example: After the Count's Ball quest, I took back the Venomous Fang weapon that I had lost at the beginning of the quest. It was equipped in my inventory for the next few pages of the game. However, as soon as I entered my next fight, the weapon switched back to the Crucifix that I had used throughout the Count's Ball quest
). I've played DQI multiple times before and this has never happened before, so I am sure that the bug is somehow related to the Pickpocket career.