Seen all of those... But... I have another route he takes that has happened to me 1 time.
Talk to him, goes out of the basement, goes left, takes another left and goes into the bedroom... then goes outside.. ONTO THE HORSE WITHOUT GOING UP THE STAIRS TO THE ROOF... then rides off... and he comes back.. goes back inside the basement... does it over again, this time going up the stairs to the roof, then goes back down, outside onto the horse, RIDES BACK AGAIN, goes to the front of the keep and just stands there moving back and forth irradically. Then goes back onto the horse and rides off, and I get the credit.
No lie. I laughed my ass off when I seen him do this. Lol.