I had the same struggle before. Have you done the Country Road event first? You need to complete that event for Logan to visit your house in Bareshade.
Okay here's the detail for Logan's second heart
- Full Moon, Bareshade's Expansion and Country Road event finished
- Talk to Logan and "Ask about his work" and then choose to help him
- Jester have visited your hut, not the one in the bareshade. I can't remember if it's at night or the morning after you "Sleep until morning"
- Visit the tavern and see the clash between Logan and Barrel.
- Go to your house between 20:00 and 3:00. This one is also luck thing, just keep going until you got it.
Hope it'll help. I've finished it awhile ago so this is the best I can remember.