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1. Finish Bandit Attack story, Bandit's Camp morale is 25+.
2. Finish Full Moon story, Logan is cured.
3. Start Bareshade Expansion story, finish the More Houses part.
4. Visit the Tavern after 20:00, that triggers the fight.

Depending on your relationship with the bandits, the dialogue will differ between Logan and Barrel.

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If you checked on Logan first when the werewolfs attacked, you have your only chance to unlock his 1st heart. And if you want to get his 2nd heart;

1. Finish Bareshade Expansion completely.
2. Finish Country Road story, gained from Ste after inviting him to Bareshade.
3. Visit Logan during daytime, witness his outburst, visit Bareshade at night and follow him.
4. Help him with work during the day.
5. Go to your house at night and Logan will visit you.