So to recap, Caboose and I are both claiming we are jailor (though most people seem to agree I am the true jailor)
Here is the game plan: I will jail Caboose tonight because I am the actual jailor. If by some miracle Caboose is the real jailor, he will jail me. It is a common tactic that a person claiming they are jailor is a medusa, so odds are that one of us is the medusa. But by the real jailor jailing the fake jailor claim, we don't have to worry about town protective going on the medusa, since they will be in jail, so no town protective will die.
Here is what I am proposing:
Lookout, bodyguard, and doctor go on me
Crusader go on Caboose
It is crucial that the Crusader does not go on me as well, otherwise he will wind up killing everyone protecting me. Also, I don't think the Crusader should reveal themself as they are an important role, unless Caboose is not actually jailed.
Anyone who is not a lookout, bodyguard, or doctor stay the hell off me