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Yup it's possible.

First install the Playback Statistics component

After that you can use the added formatting fields shown here to make a new custom columns

for showing play count the pattern is: %play_count%

I'M NOT GIVING UP ON YOU DAMNIT.

There must be an app that rips the metadata from the aiff files. Alternatively, http://www.xdlab.ru/en/ or http://www.mp3tag.de/en/, not sure if they work with aiff. But they should be able to automatically gather metadata based on file names.