Your first mistake is admitting you were pocket dipping!!!!!! Simply run away and shout "You can't prove noffin!!!", it is foolproof.
Next!! The best place I've found to pickpocket is guards!! I've robbed almost all of the good cities so far (and the evil ones soon)....and it is actually pretty good moneys. Bonus if you can get a cleric to come by and rez all your bodies when you are done :3
Shields sell for 1-2pp (qeynos shields being great targets).
Problem with guards is it is a one time thing....so finding a place with guards that die is a good idea too. Like Karanas there are guard towers. So you can go find giants, pick pocket their gold, then train them into guards and pick pocket their shields as they fight. Then, the giant wins, run it to the 3rd guard (take his shield too), and he usually wins...but sometimes not and the giant is low enough for you to finish off with it running.
Either way, you get everything reset soon enough for more shields and more riches!! (qeynos kite shields sell for about 2pp each!!).
I've been on a journey to find the best pickin pockets spots....I've discovered some interesting secrets. For example, apparently you can pick slimes. So lately I went to wakening lands in the geonid caves. You can't pick pocket the geonids, BUT there are slimes in there which the geonids agro on (giving you an easy source to respawn infinite pockets with).
I didn't have any luck with the few slimes I tried, but I might try again later (apparently they can have nice gems).
Also, FYI, drakes in skyshrine are pickable (drakes in general are humanoid for some reason).
I also have some more ideas of good pick pocket targets...but those are secret.
Pick pocket will be a path to riches!!! Richessssss!!!
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