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Remember that decision that you cannot change back in the bandits event? That is the time when Logan can Bottom or Top? Maybe you need to make him bottom, and take potions, or f**k some people so you receive the trait of a Top, then maybe it will activate? I am just speculating but try it out.

I think if you encourage him to bandit camp the event" I owe you a beer" itself wouldn't available...

I owe you a beer does disappear if you have bottom logan.