Spoilers in clear text. Turn away now or risk having the experience spoiled.
I went to Highpool and cleared everything, picking up various quests along the way.
Talked to Sean Bergin and got the quest to kill the raiders in order for him to consider working with us Rangers instead of the Red Scorpion Militia.
Circumnavigated the Highpool "residency" area at the top, and released Vulture's Cry and added her to my team. Helped the man with the dog, cleared the sewers, helped the man with the burning house, Talked to Kate Preston and learned about the upcoming election and how I had not helped enough people yet in order to sway them to her side.
Now Sean is pissed off because I have released Vulture's Cry and he won't talk to me.
I think to myself; I'll kill those pesky raiders for you and we will be best buddies again, and I do so. I also return the gun to the woman in the house on the lower levels, but Sean still won't talk to me, and Kate says that I need to help more people.
It seems I am in a loop I cannot get out of because I released Vulture's Cry and Sean did not like that; now he won't talk to me so I cannot hand in the quest for killing the raiders, and so I have not helped the people of Highpool enough to hold the election.
I have since played for hours and hours trying to find more ways to solve this, but I think I am stuck.
Will I have to reload that ancient save and help Sean first or is there a way?

I went to Highpool and cleared everything, picking up various quests along the way.
Talked to Sean Bergin and got the quest to kill the raiders in order for him to consider working with us Rangers instead of the Red Scorpion Militia.
Circumnavigated the Highpool "residency" area at the top, and released Vulture's Cry and added her to my team. Helped the man with the dog, cleared the sewers, helped the man with the burning house, Talked to Kate Preston and learned about the upcoming election and how I had not helped enough people yet in order to sway them to her side.
Now Sean is pissed off because I have released Vulture's Cry and he won't talk to me.
I think to myself; I'll kill those pesky raiders for you and we will be best buddies again, and I do so. I also return the gun to the woman in the house on the lower levels, but Sean still won't talk to me, and Kate says that I need to help more people.
It seems I am in a loop I cannot get out of because I released Vulture's Cry and Sean did not like that; now he won't talk to me so I cannot hand in the quest for killing the raiders, and so I have not helped the people of Highpool enough to hold the election.
I have since played for hours and hours trying to find more ways to solve this, but I think I am stuck.
Will I have to reload that ancient save and help Sean first or is there a way?
