I'm wondering if you will be to able steel better things once you increase the pickpocket skill or does increasing just higher the chances for you to suceed? For example I tried to steal the quill pen from Dhall, but I just got the message from the NO that the target didn't have anything to steal.
Also would I like to know if the skill affects your alignment, like makes you more evil and/or chaotic once you use it.
It only affects the chances of success. You'll find some nice things in the Sensate Palace, and a lot of junk down in the Warrens.
To the Righteous belong the fruits of violent victory. The rest of us will have to settle for warm friends, warm lovers, and a wink from a quietly supportive universe.