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FextraBot

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Kickback is pretty worthless if you ask me... lol...
Not when you stack 5k+ bounty I can tell you that. You get a lot of skill points but money is limited.
?

Only 5k? Use swiftly forgotten. It will be cleared in 12 hours.
You also gain a point for laundering stolen items and you can launder the same number daily as you can sell to the fence. This doubles the rate at which the skill line levels.

Personally, I sold the expensive items to the fence and laundered the cheap stuff if it could be used by my provisioner.

There is a warehouse by the docks in Vulkhel Guard that's full of barrels to be robbed and no NPC's to see you. After emptying the place, log out and in again and all the barrels will be reset. Rinse repeat until you have enough items to fence/launder at the local thieves den (which is very close). Do this daily and you'll be level 20 in a few weeks.
What works for me to get a lot of points in Legerdermain daily is to do this:

Travel to Daggerfall, Glenumbra.
Unlock and Loot houses in order:
1. Lavergne House
2. Gane House
3. Stogrin House
4. Landreau House
5. Jeran House
6. Hastien House
On the map follow the Yellow path to get to the houses, black path are
guards and red path is where to run if you get caught by guards.
Fence expensive items, launder cheap ones and sell to merchants.

https://i.imgur.com/DMCyBix.jpg
Image of the map
Making a level 20 Khajiit with full of these passive perks be perfect for providing gold to the rest of 7 characters. I’m going to do it now. Thank wiki.