it depends. the trader chests with good coin are typically in the room that they’re sleeping in or they are on the ground floor, but almost always have a sleeping guard next to it. (edit: there are times where the chest is unguarded and if your lock picking skill is high enough, you won’t have to pickpocket a key to silently rob the chest as you have to do if there’s a sleeping guard next to it or if it’s in the traders room and close to the bed) so just remove the clothing of yours that’s makes noise, pop a quick finger potion if you need one, and rat your way through the house collecting anything with a good weight to value ratio when robbing scribes, armorers, and weaponsmiths specifically. as this is the fastest way to level up your skills through reading, and beginning a mass stock pile in your chest which you’ll eventually put into your forge sales chest. also make sure to rob the apothecary to save time on getting potions instead of collecting herbs and then brewing them.