It's not just with Willie one Eyed for me, its almost every scripted scene , I need to keep re loading and trying different hacky methods to advance these.
Sometimes saving in the middle of a scripted event of these break scripted scenes entirely making it impossible to progress the quest you were doing, unless you re load a save that wasnt the one you just did in the middle of a scripted scene.
If a random NPC in the world attacks a character involved in a scripted scene with triggers it can also break the scene if you don't take care of the hostile NPC fast, these happened a lot in the missions where I have to go scout with ophelia and jammer or just with ophelia.
The only way for these to progress(again, for me, not sure if everyone else have this) is if no object/npc gets in the way and scenes work out flawlessly. That is hard to make happen because Fallout 4 is so dynamic, especially my setup, I can have a scene one minute but the next re load a deathclaw will come in claws blazing on the same scene , random encounters, and stuff.
Im thinking gath did something to the dialogue in this update that just f*ed it up for me because when Conqueror first launched I wasn't having these kind of problems, and I still don't on early questline missions, its just when I get to the new content missions involving ophelia and the new characters where stuff is just too broken.