Tell Plugin Manager to delete specific files

Is it possible/weill it be possible in the future to somehow tell plugin manager to delete specific files when updating?

I am thinking of a case where a menu entry links to a file, but the update removes the file and the menu entry points somewhere else - there will be a period of "confusion" until the menu cache is cleared.

I do understand how any manually added files to the folder may be necessary and their deletion problematic, so this will need to be specific where an update somehow informs plugin manager that the file needs to be deleted.