The game should simply allow multiple long rest events to occur in the same rest.
Why would it be impossible for a "hey lets romance plotflag" conversation and getting woken up by Scratch and Birdbro dealing with nightmares to happen in the same night?
The answer is that there is no reason why.
Once you get around to a long rest, every queued long rest event should happen. All of them. Regardless of how many.
