It seems to me from my experience with the companions and the quest line, that this quest line and the people involved in the guild and quests are very buggy.
I married a person from the companions, and after having her follow me then dismissing her I can no longer get a follower.
I have the same quest from a member that fails each time because I have a ghost follower that will not go away. Several other people have reported bugs with the followers, and companions quests.