I got an upload message, clicked on the link and it just took me to the top level directory of the files section. Some exploring showed that the file had been very slightly renamed, same directory. While I understand the missing file behavior, I think it could be confusing or even scary for less tech savvy folks.
What this suggestion request is that the old link as published act as a soft link to the new location and transitively so. If someone wants to use a soft link filename for an actual file, it can be deleted in the same way that any other file is deleted. E.g., much as UNIX filesystem links work.
PG&E Delenda Est