I don’t imagine 9.1 to be Sylvanas’ raid.
I’m almost certain the Jailer goes before she does.
Which, honestly, could be this patch. Zovaal is downed by her betrayal, we get the setup for another villain, and we get the setup for Sylvanas’ downfall. The Jailer feels much too… impersonal in the actual Shadowlands story to really be a worthwhile expansion long villain.
He doesn’t show up outside of the opening quest, as far as I am aware, in 9.0. We just get murmurs of his power, and nothings very ominous or intriguing about him. What interests me is the villain who is nowhere to be seen, period. Sylvanas also shows up once, and is mentioned EVEN less than the Jailer.
While I see Sylvanas dead at the end of Shadowlands, I don’t see it so soon. And honestly, I could see this patch being in a realm of death being invaded by the Maw. Maybe the one with the pagoda gateway. And the raid takes place there, with the Betrayal of the Jailer being the cutscene.
Then Sylvanas runs back to Azeroth to cause havoc, we defeat her forces.
Final raid in the Maw, where we imprison her with Arthas, Neltharion, and all black hearted monsters like them.
Those are Sint thoughts.