Yeah you have to be committed to pickpocketing. Really its a bad skill except when you finally get to 70-80 points (including sneak of course), although pickpocketing elwood is probably the one exception where its useful. I think there would come some point, where you're finally able to sneak and steal easily, but even at level 12 I haven't reached that yet! (and I found some leather armor that gives +23 to stealth). Oh well I still stole a bunch of good stuff, so it was fun and I think probably worth it later on.