Yes, you need to complete Bareshade Expansion. Be sure to "really" end the country road storyline (you should see the location (new road) if not visit ste more or less between 17:00-20:00 to see their first meeting.
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.
No, but if you have bandit's morale is at least 25 and, after entering at least 5/10 times the bar, nothing happens, is safe to assume it already happened. I forgot to mention that to trigger the "I owe you a beer" event you need one heart and forty Logan's likes and to enter the house, you don't need to sleep.