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stack sleight of hand and other buffs
don't be greedy as stacking that stuff only goes so high you can still fail pretty frequently tryign to steal a 12+ item (or get as greedy as you want if you want to re-load your save a billion times to steal everything)
use the left shift key to see their visibility cones then when its clear lock it into turn based mode.
use turn based mode so patrols don't walk past or the npc doesn't turn around
dash away in stealth while still in turn based mode then deactivate it and run further away before they realise they have been pickpocket and search the surrounding area (quickly teleporting to a nearby way point is easiest) then just approach them slowly again and let them finish their search from a distance before you go closer again
When NPCs are in problematic positions, you can do the following, and probably more with some creativity: put them to sleep with a spell or potion, cast fog or darkness to obstruct line of sight, distract them with a familiar or minor illusion to lure them away.
NPCs will notice an object was stolen if it was in plain sight, but probably not if it was in a container. If they do notice, but don't know that it's you, run away. They'll pin it on you if you stick close to the scene of the crime. If you were seen committing the crime, you can use Disguise Self to slip away, or if you were under the effects of Disguise Self during the crime, you can drop it to cast off suspicion.
And you put them in a Hide position so the NPC that is being pulled away can be pickpocketed. Make sure to turn it on Turn Base Mode and pull your other Party members out of range. Then you just simply quick save and start running them pockets. Make sure you get all the lower roll required items. And once you get that done, save and start working through the higher save items. And Save before each one and reload if you have to. Though when you save you'll have to do it again after you reload since you won't be able to pick the pockets.
Rinse Repeat. And make sure you take your thief in turn base mode and leave the area of the person you robbed and hide it out then get out of turn base mode and repeat the steps.
Damn, that is evil.
1. change appearance to soemone else via spell or scroll
2. stealth
3. pickpocket
4. change back
Disguise Self, steal, run away, steal, run away, if you get caught just go to jail and break out and loot the evidence/equipment boxes and then remove your disguise, add a new disguise and do it all over again till you get whatever things you want.
Method 2:
Have someone use "Hold Person" on the vendor, steal to your hearts content, whether they "catch" you or not they're held so they won't be able to do anything, such as turn and see who stole. When you're done just run away.
Method 3:
Cast Fog Cloud/Darkness and Silence over the vendor you want to steal from.
There's a bunch of ways to get Advantage on slight of hand and stealth checks, easiest is probably "Enhance Ability" cleric spell, lvl 2 spell, and just select Dexterity. Keep the cleric well away from both the thief and vendor you want to steal from.
https://www.youtube.com/watch?v=kGbLSKtMkLk&t=170s
It doesn't work.
Fog cloud to block lines of sight, or minor illusion to turn NPCs away, entering turn based mode to make sure nobody turns back, then using "go to camp" to get away does though.
You just need to be careful when you re-enter the area (after fast travelling from camp, not just using leave camp) to stay away while the NPCs run through their search animation.