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you get his first heart automatically? If have visited Bareshade with him and return to Farmstead, you will gain his first heart, and only then the Country Road story is triggered.

I already get the first heart and you said after finishing the country road quest go straight to ste farmstead and I will find Logan there but I can't find him there. Is there any condition need to be met before visiting ste house after country road quest do Logan be there? 

it's rng... But I do always find him there for that event after 15:00 at least.. hope that helps

so it's repeatable?