Oh yeah after finishing country road you might have a hard time figuring out how to get Logan's second heart, so after you finish that event, try looking at the devlog 0.31 there will be some guidance there for his second heart
The clash with barrel is just the event where Logan has a discussion with barrel at the bar because barrel is pestering a girl there, and the I owe you a beer is the event where you get his second heart :P
