I can't activate "I owe you a beer" even with all the requirements met, and I've been trying to activate it for a while. Are you required to have only 1 heart with Logan? Because I already have 2 because of the werewolves' fight with the swamp creature. I've tried sleep, relax, rest, getting in and out of the house in Bareshade, if anyone can help, I'd really appreciate it. Maybe it's just bad luck and RGN doesn't want to cooperate.
The same thing is happening with me. I've done it a past update before but for some reason I can't do it in the new one. I haven't done the new quest with him however I have done the investigation part and fought the swamp werewolf. Maybe it's a glitch with that or just a normal glitch, which is really annoying. I'm going to experiment a bit and maybe do a reset, If I find anything i'll post it.
I did it randonly on my first gameplay, didn't even knew it was an issue.
I think it happened before I spent time with him at the weekly festival in Bareshade (I remember something about the MC mentioning the new house in town and asking him to come visit anytime, but it can be just my imagination)
From what I saw, you need to already have seen that scene with him and Barrel at the tavern and maybe try giving him gifts. Rose sells an item called top something you can give it to him.