I think adding a /trade feature in Prison would be cool, because it allows players to trade items for money, which would make the economy more useful.
While you can already drop the items to other players, other players can come pick items up, and you can scam players as well, so by making a trading feature, it would reduce the risk of scams.
I think it should work through commands (/trade <username>), and players should be able to trade with their coins as well, to make them "more useful".