When did Layout become a dumpster fire of stability issues?

I agree, a list item for each individual label can be an obtuse solution. The trouble I often have is when I need to select something that is underneath another object.

Vectorworks solved this problem quite elegantly with a “Select Coincident Objects” option in the right-click menu: it would populate a sub-menu with a list of the objects layered where you clicked. When you hovered over each object item in the sub-menu, it would highlight the object’s outline.