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I was thinking about creating an army of GKs with the LotD as allies, but I'm not sure if that would work fluff-wise. Does anyone know of any occasions where the GKs accepted the LotD or something of the sort?

I'm not too familiar with 'the damned' but I know the GK have been known to work with some otherworldly forces and tolerate them in the past, namely the Haunted Knights of Mortain and the perpetual nature of Anval Thawn. Not to mention Draigo being literally one with the warp. Something tells me that under the right circumstances, the sons of Titan could learn to set aside their suspicion in the heat of the fight.

There used to be a rule that you weren't allowed to field GK if you had deamons of any kind, including deamonhosts. This rule is gone and the Grey knights are best buddies with deamons according to the codex. The same can be said for the legion if the damned.

Honestly I don't think there's a good answer except "whatever the writer was thinking at the time" so go nuts.