My question is in the title, tips for robbing NPCs blind? (Perhaps literally— would darkness or fog cloud spells work well in this context?) I’m currently playing a wood (half-)elf bard with sleight-of-hand and stealth proficiencies, and high charisma/persuasion to talk myself out of trouble. I’m planning on picking up the gloves of thievery and smuggler’s ring.

So, what strategies do you use to make your pickpocketing as effective as possible? Who are some of the best NPCs to pickpocket?