I think pickpocketing and reverse-pickpocketing would be involved, given his love of stealing from the Skaal and his status as a trickster/corrupter.
An anecdote, that might be the kernel of another idea:
Last week I was sneaking through Liar's Retreat through a camp of bandits looting as I went and became over-encumbered. So after checking to make sure I was hidden I dropped some armor I was carrying (Glass Boots are what I remember most prominently, but I'm pretty sure there was some other stuff involved too). Then, as I started to walk away, one of the bandits came over and picked it up, as NPCs often do. The strange part came next: as he was picking it up, another bandit let out some kind of pre-scripted phrase ("no way, that's mine!" perhaps?) and attacked the one who'd picked up the boots! I've been playing Skyrim for three years and that's never happened before. It was like a tiny Fury spell. I don't know if that happens reliably enough to make a whole build out of that, but it would definitely be a fun trick for a character like the Greedy Man, who's just out to cause chaos.
I think pickpocketing and reverse-pickpocketing would be involved, given his love of stealing from the Skaal and his status as a trickster/corrupter.
An anecdote, that might be the kernel of another idea:
Last week I was sneaking through Liar's Retreat through a camp of bandits looting as I went and became over-encumbered. So after checking to make sure I was hidden I dropped some armor I was carrying (Glass Boots are what I remember most prominently, but I'm pretty sure there was some other stuff involved too). Then, as I started to walk away, one of the bandits came over and picked it up, as NPCs often do. The strange part came next: as he was picking it up, another bandit let out some kind of pre-scripted phrase ("no way, that's mine!" perhaps?) and attacked the one who'd picked up the boots! I've been playing Skyrim for three years and that's never happened before. It was like a tiny Fury spell. I don't know if that happens reliably enough to make a whole build out of that, but it would definitely be a fun trick for a character like the Greedy Man, who's just out to cause chaos.