Idronea Elval in The Rift

The safest, most methodical way to run through the repeatable Thieves Guild Plucking Fingers, Idle Hands, Under Our Thumb quests is, first, to equip oneself with The Blade of Woe by completing the initial Dark Brotherhood quest. Instead of sneaking about looking for a string of victims, with possibly a bounty on one’s head, pick out one or two easy marks in a safe area and work them repeatedly. Citizens are good for three successive pickpockets. After that, rinse and repeat: assassinate them so they respawn with full pockets again.

When you are starting out with low pickpocket skills, you’re better off disposing of targets after one or two successful attempts than trying for the full three at lower odds. If you kill them early, when they still have goodies in their pockets, you at least get to loot their corpses and take something for your trouble.

Though this requires a bit of immediate patience, waiting for your victims to respawn, it often amounts to time well spent waiting in safety for the bounty on your head from mistakes to wear off. Overall time and bounty savings can be considerable.

I prefer to target fishers. Nearby water often affords the opportunity for a bit of fishing while waiting. And a jump into water usually enables you to evade angry citizens who detected your not-so-light fingers, without needing to kill them and seriously raise the bounty on your head, or to run helter-skelter through streets into guards.