For visibility, I've done loads of other crimes:
- Bootlegging 100.00
- Graffiti 100.00
- Search for Cash 100.00
- Shoplifting 100.00
- Burglary 97.41
- Card Skimming 73.63
- Racing 15.67
- Hunting 11.40
- Reviving 10.69
- Forgery 1.12
- Arson 1.05
But I can't ever get pickpocket above 5. I only go for the safer targets as detailed in the Wiki post, I've read a few guides too. But no matter what, I eventually hit a crit fail and it wipes my level back to 1 again. I've given up on it twice now, and may just not bother at all but I honestly don't understand what I'm doing wrong :(