The official FAQ says:
Q: If the a player is required to choose a character to send to the “Brig” or “Sickbay,” can he choose a character that is already there?
A: No. He also cannot choose a revealed Cylon player, or “Helo” before he is on the board (due to his negative ability)
Oh okay. I see. The cylon part actually has been ruled on. But can I read that ruling to mean that one can never make choices within an event or failed skill check consequence that prohibit him from satisfying the demands if different choices would have allowed him to satisfy those demands? I read this to be a categorical rule about all conditions needing to be fully satisfied if they can be. Some have suggested that's an overreach. That's the question that I seem to remember was left dangling in a thread a few months back.
At any rate, thanks for digging this up. I had forgotten that the cylon thing was explicitly stated in the rule.