For all but the last one it seems like you'd need an in-depth knowledge of the gatekeeper's psyche and personal life.
Of course. How else would you know which horrible, horrible things to say? (I also have in mind things designed to get a more visceral reaction from the gatekeeper, e.g. graphic descriptions of violence. Please don't ask me to be more specific about this because I really, really don't want to.)
You don't have to be specific, but how would grossing out the gatekeeper bring you closer to escape?
Update 2013-09-05.
I have since played two more AI box experiments after this one, winning both.
Update 2013-12-30:
I have lost two more AI box experiments, and won two more. Current Record is 3 Wins, 3 Losses.