For failing the courier contract, Rens to Jita. The collateral was worth well more than the few containers and the shuttles in it. (Also, the few times it took for me to get a bite on this scam, too. Total “invested”, roughly 4 million. Net gain: 21 million.)
I think the “fine line” here is that the reward has to be less than a million to keep the bots away from the courier contract.