Just how many daggers and suits of leather armor can the halfling druid afford to buy? And why would he buy that many to begin with? Does he have a market for this stuff?
Aaron lives right next to goblins. I’m sure they’d like their stuff back, even for a fee.
As for the vendor approval flavor, I picture it the opposite as Crimsonrider. I see all vendors as crooks to be beaten at their own game. I can see the both the real price and what they’re charging. They’re no angels.
Having high charisma means being able to defuse the predatory vendor tactics, while low charisma chumps get the extended warranty.
