Something weird happened to me recently. Even though I've played Ps:T many of times, 3-4x. I just often learned why I never had any money in the game! You must pickpocket EVERYTHING, once you have Annah.
The problem is, I loved getting SO rich on Baldur's Gate I and II, but mostly just on good alignment in BG:II.
Well, I made so much money pickpocketing in this game. The problem is, it wasn't very good in BG:I&II like I think it is in Ps:T. I also like that some shops you can steal from and others you can't.
I rarely remember stealing much of value from Bg:II.
So, that's my beginner's tip. Pickpocketing was lame in BG, but is actually fun in Ps:T. Agree?