Logan can have, as far as I know, 3 hearts. The scene in the forest everyone is talking about is only available if you choosed Logan's route during the Full Moon event (if you choosed to run after him over Bernard)
That guy you mentioned I have no ideia. I don't even knew how I unlocked my dialogue with him. Maybe try taking a walk there at night?
About the gloryhole I don't know either since I've spend hours there and nothing happened (just some poeple here and there)