The Bandit's Camp morale must be 25 or higher, Barrel will visit the tavern.
If you have completed the Bareshade Expansion and Country Road, Logan will have a clash with Barrel the next time you visit the tavern.
All you need to do is help Logan out (talk) when you visit him and he says that he'll owe you a beer.
Lastly, visit your house in Bareshade in the evening and Logan will show up.