Finish Bandit Attack, Bandit's Camp morale at 25+, 'More Houses' part done in Bareshade Expansion, have Barrel visit you during the night when you try to sleep (8hrs), and Harold must be at 20+ likes.
Ah if you don't know about your 2nd house in Barrshade rven then that means you haven't started Bareshade Exoansion.
Just focus on finishing Bandit Attack and Full Moon, you can see where you're at when you check the questlog, the scroll icon.
Oh if you do have finished Bandit Attack, check their camp icon on the world map you should see on the left side of your screen what their morale currently is... just keep them satisfied.
Bear? I think you meant beer :) The scene to get the beer is also the same scene where he visits your home in Bareshade and where you get his 2nd heart. There must be some prerequirements done in order to unlock the event stated previously;
Have Logan discouraged to go to the camp, check on him during the werewolf attack instead of Bernard, finish Full Moon, Bandit Attack, Country Road (free Ste from Vicoria's and let him visit Bareshade) and the 'More Houses' part of Bareshade Expansion.
By finishing Bandit Attack you already have unlocked the Bandit's Camp, make sure its morale (seen on world map) is 25+. ln the evening when you visit the tavern Logan will have a fight with Barrel.
Just in case help Logan out again with work for the beer that he will promise, last thing to do is just click your new home in the evening which could already trigger the event.
... I don't understand the second part of your comment, so I'm not sure what you're saying.