Hi Nyan :3
The biggest problem with stealing is, that each time if you get caught your reputation will drop by -200 (or maybe -100, I don't remember). And with -1000 you will be shot on sight by guards as far as I know. Also there is no way to increase reputation for now... So I wouldn't try stealing from players in big towns with less than 250 stealing... There is some bonus for stealing at night AFAIK. You can find some places where reputation doesn't drop or where it doesn't matter and use it for training with NPCs.
But anyway, I suggest to make a test build and test everything yourself, especially the reputation thing, before you make a real character.
Life is easier for lockpickers these days, because you can steal cars on desert...