I think the requirements for 'I own you a beer' event is..
- Location: Your own 'house' at Bareshade, not your own hut near a forest.
- Time: at night (after 20.00).
- Bareshade: You need to finished all Bareshade upgrade event.
- Logan: You need to have his 1st heart and also his enough likes (I think 95 is more than enough for it), you also need to help him during a day (I don't know how many days you need to help him since I help him everyday when I enter to Bareshade (even if I can't get his more likes from doing this but I just want to see his face)
- Other conditions: You need to finished Country Road event and a fight between Logan and Barrel.
- Your own luck: This event is RNG (because first time when I'm sure I finished every requirements but it doesn't happen and when I re-enter a house again and it happen.)
If you sure that you meet and finished every requirements in 1-5. So I think the real problem is the last requirement...