Posted this not long ago, so I'm reposting it here because this question pops up a lot.. (and making it better to understand)
- Finish Bandit Attack story, Bandit's Camp morale is 25+.
- Finish Full Moon story, must've checked on Logan first!!!
- Start Bareshade Expansion story, finish the More Houses part.
- Visit the Tavern after 20:00, that triggers the fight between Logan and Barrel.
- Finish Bareshade Expansion completely.
- Finish Country Road story, gained from Ste after inviting him to Bareshade.
- Visit Logan during daytime, witness his outburst, visit Bareshade at night and follow him.
- Help him with work during the day.
- Go to your house at night and Logan will visit you, invite him in, refuse to have sex.
The dialogue will differ between Logan and Barrel depending on your relationship with the bandits, just like your relationship with the werewolfs when Logan visits you, his dialogue will differ as well.