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During the bandit quest you have to stop him from going to the camp otherwise he'll be on the bottom Logan path which has some good scenes but for story purposes it'll lock you out from his romance quests and Werewolf event you have to go after Logan when the village is attacked at night otherwise you will be locked out of his romance quests as well. Don't worry going after Logan doesn't lock you out from Bernie's romance stuff cuz I like him as well. Definitely take advantage of the save system before making choices as well as for one time events or scene's you want to see again later on.

There is also the option of getting Arion to have "fun" with her in exchange for letting her first prisoner go. Honestly its the easiest way to do it from my experience you just have to have Arion's like high enough I think you only need around 20 something like but I can't remember. 

From what I remember from when I played you have to talk to Scar before you leave then you can use the snow clothes and the warm potion to travel across

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 can't seem to trigger Logan's "I owe you a beer" I've done all the requirements (1 heart, over 40 like, finished farm road, all Bareshade upgrades, helped him work, and seen the Barrel argument) maybe my rng sucks. Update .46.