Regular Logan only has one scene that has a good amount of requirements. also you need to be one heart from him before any of this can happen.
Those requirements are
1. All of the bareshade expansions done
2. Country road complete
3. Seen the him yell at barrel in the bar
4. I believe it's just sleep at the new home you get from the expansion event.
It doesn't seem like a lot but two of those take a good amount of farming if your not gonna use the chest menu, and the first one also is a lot of going home and sleeping or doing literally anything else.