My biggest bankruptcy was when the jester asked for 700 gold, I was about to refuse, but then my cat stepped on the ' Y ' button on my keyboard... I was at - 675 after that...
I accepted his quests and he nearly always came back with 250 gold. I accepted the thief all the time, after all it's just -5 happiness. But then again, I did NOT give her the key to the gate. She got arrested for attempting to climb over it later.
