Are you saying that you can only anchor an element to one of its ancestors? Can CSS really not define positional relationships between siblings (I'm used to Apple's Auto Layout)? If so, couldn't you add an additional outer container that doesn't crop its contents to its bounds and anchor the dropdown to that?
If you have a trigger inside a nested scrollable region, and the popover pops out of this region, then if the trigger is scrolled out of view the popover cannot be anchored to it anymore.
This runs counter to the behavior of it being anchored to a parent container.