Well, I had tried visiting the bar again and again at night but Barrel never showed up. So I'm wondering is it too late for this to happen or do I need higher lewd fame. Bandit morale is higher than 25
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.