bottom Logan locks you out of his romance route. you can't romance him in that route. you can only romance Logan if you discourage him from going to the bandit camp and you'll get his first heart if you choose to help Logan instead of Bernard the night the werewolves attacked bareshade.
you have to have met Ste and saved him from Vicoria's prison first. Find his house in the farmstead and bring him to bareshade. Make sure that Korg lives with you. after you brought him to bareshade, the quest will be available.
yes. as I said previously, bottom Logan route completely locks you out from romancing him. you won't get a single heart from him in bottom Logan route.
I did. it also took me awhile because I didn't know about the country road quest at first and boy was I happy when I finally got it. and I think I'm caught up with the game atm. nothing to do but wait for the next update.