you go to sleep at night at your house in bareshade and, if you've read logan's fight with barrel at the tavern, barrel should show up at your house just as you're about to sleep.
Have you already figured it out?
Anyway, it's with NORMAL Logan, finish the Bandit Attack, Full Moon, Bareshade Expansion (More Houses) and Country Road.
Once you have done that, Bandit Camp morale must be 25 or higher, helped Logan out with work, then visit tavern at evening.
(Click on your house in Bareshade and it should already trigger a visit scene with Logan, if not then try again.)
Barrel's case is easier, just get your new home, have morale at 25+ and sleep at night for 8hrs (mostly triggers in weekend)