I would put a note into a field you don't use, using a word or phrase you wouldn't use in another field (such as putting XXX, FIXFIXFIX, etc) and add that field to the search index. This will allow your assistant to search for flagged files, and will allow you to easily flag them using the focus key e when browsing. You can even embed that information so that the flags can move with the files.
Josh Ritz
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