There isn't a single instance that I've come across you have to have someone in conversation with to make them able to be robbed, I'm a thieving mother fucker.
Level 3 rogue/thief with 2 actions you don't even need to sneak first.
-Go into turn based mode, locks their movement
-If people are watching, have one of your other chars cast fog/darkness/dark arrow, if you literally can't then you may have to do that first before turn based mode since pickpocket uses up an action point
-Sneak
-Rob blind, pray for no 1's (or be a... halfling? who has lucky to reroll those). Turn off the feature that tries to normalize dice or you probably will roll back to back 1's even with lucky cause its bullshit rng.
Rogue's make the best choice cause you can (from the getgo) pump up their sleight of hand and stealth proficiency obscenely, and later on you can multiclass something like 3 rogue for the 2 bonus actions & 9 monk, rob and beat the shit out of those damned merchants.
Level 3 rogue/thief with 2 actions you don't even need to sneak first.
-Go into turn based mode, locks their movement
-If people are watching, have one of your other chars cast fog/darkness/dark arrow, if you literally can't then you may have to do that first before turn based mode since pickpocket uses up an action point
-Sneak
-Rob blind, pray for no 1's (or be a... halfling? who has lucky to reroll those). Turn off the feature that tries to normalize dice or you probably will roll back to back 1's even with lucky cause its bullshit rng.
Rogue's make the best choice cause you can (from the getgo) pump up their sleight of hand and stealth proficiency obscenely, and later on you can multiclass something like 3 rogue for the 2 bonus actions & 9 monk, rob and beat the shit out of those damned merchants.