Who are you talking about? Most characters in the game can be pickpocketed, if not all of them.
If you're undetected, no-one will take any notice.
I tried it once. the money doesn't get added to her inventory.
Oh, I beg your pardon. Forgot about her, haven't used her at all.
I'm pretty sure you can, I don't see why not? You'll need the necessary perk. I always pickpocket the money back from the Archery trainer in the Ratway. When I fail, he always forgives me.