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Maybe there is a way to unbug it somehow and somebody will figure it out
I think I had something very similar.
I brought the horse back literally few steps from him, and I saw the green check mark appearing, I moved the horse back a bit, the quest re-updated without check mark and me being unable to speak to him. I had to get the horse again very close, green mark was back, and so was the option to talk and progress.
I managed to finish the mission. You have to ride his horse very close to him, almost on top of him. Then the part is completed and you can talk to him.