pickpocketing is an absolute bitch to level up. practice on bandits I guess, so if you get caught you were gonna kill them anyway to whatever. i just level it to get that perk that massively increases your carry weight (100 i think?) but the huge amount of jewels and money you get out of it is well worth it
I actually just leveled it up a few levels because of a really bizarre situation
A dragon started attacking the town I was in, but flew away when it got weak, so I chased after it and killed it
Three random guys ran up and stared in awe at the skeleton, and I stole half of their stuff while they were distracted, killing each one when they finally noticed me while the others completely ignored us
Turns out there was a contract on one of them that says they were hired by someone to get revenge for me stealing, but looking at a dead dragon was apparently more important