To trigger a clash with Barrel you must have above 28 the morale of the bandit camp, it is achieved by giving money to Jasper and doing the mission of the day that Jasper has for you, after that you go to the bar at night you enter and leave you will see a dialogue between Barrel and Logan that dialogue ends, the next day he sleeps at Barashade's house at night at around 8:00 p.m. you will have the final event with Logan leaving that part to score points with him