Yeah, I saw that after going in and out a bit. So all I have to do now is fiinsh renovating Bareshade?
... I say like it won't take A While.
Yes, the event should happen at evening. Be sure to not sleep with him, otherwise he will hate you. In addition (is not a requirement) equip "lucky charm" (invite Logan at the fair and play the guessing game), so you unlock a little thing missable (don't redo all the game just to obtain lucky charm, it unlocks a cute thing, nothing more.