- How the hell does Forged in Steel's Michael, who has the mind of a child, survive as a vampire?
- How did Gordon Keaton, Son, Ballard, and other characters like them not go insane despite having Humanity 0?
- It was Early Installment Weirdness where Humanity 0 didn't necessarily mean you became a wight but just that you were irredeemably irrevocably evil.
- How was Kevin Jackson able to become Prince of Chicago despite his age? He's not even an Ancilla or, if he is, he's just barely so.
- Money, power, and the fact that the Prince in Chicago is a Puppet King position for the Primogen. Or, Helena, in this case.
- Kevin Jackson benefited from a perfect storm of events with a weak prince in Joseph Peterson, several of the other candidates suffering catastrophic failures (Ballard getting caught in a porn theater and losing his personal fortune), and a lot of the Primogen being Beckoned or killed off. As such, he was left as one of the most powerful Ventrue in the city as well as Lodin's direct descendant.
Headscratchers / Chicago By Night