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@phssthpok - for one library I do similar to theducks, I have a custom column called Last Action Date. There's also an associated custom column with a fixed set of values called Last Action.
I also wrote a utility, for each book it determines latest file modified timestamp and filetype, which it writes to a CSV. I then use the Import List PI to read the CSV and update a couple of custom columns - Latest File Type, Latest File Date. Of course, the columns are almost never up-to-date (normally I don't even display them), I don't often need them, so when I do I run the script and Import List. I found using a template made calibre very sluggish - but that may have been in version 1.x.
My utility is written in C (because that's what I know best), but the same thing could be done in a script in two shakes of a lambs tail - but I loathe scripting languages.
BR
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