Im pretty new and started at the very low crimes. I worked my way up to pickpocketing (Left out jewerly) but now I stuck there. I only can pickpocket the hobo but I fail at everyone else. The hobo though works. I successfully stole from him like 100 times now with like 3 reds in total.
Why cant I steal from anybody else?
How much nerve do you have? Each time it increases, it's a good symbol that you're capable of higher level crimes. IIRC, before 20nnb, it's best to steal Thriller DVD's, then 25nnb thorough robbery (never get a red result and gives best crime exp at that level), 30nnb, stealth virus', 35nnb, arson warehouse all the way up to 45nnb, but at 40nnb throw in a kidnap mayor every here and there.
You may want to do more shoplift > jackets, maybe a few hundred more, before trying to pickpocket. When I was starting out, I stole a lot of jackets before moving up because I was scared of red results.
Before I came to pickpocketting I did every crime atleast 30 times. Im steal from the hobby for a few weeks now.