Quite a lot. I know how to use ReorderableList on a custom inspector (Editor), but neither the Add or AddDropdown callback seems to support the feature pictured above out-of-the-box or I might be missing something.
I mean you would be handling the popup yourself. You’d hook into the callback, and when invoked, open a popup editor window, likely passing it the collection’s serialised property for adding to when the selection/input is made.