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Staying Organized
You don't need to select all the tracks you want to delete, add a comment, search for the comment in the library, and then press Cmd-Delete. Just select them in your playlist and press Cmd-Opt-Delete. This will remove them from your playlist AND from your Library!
Staying Organized
I just submitted this a little while ago as a new "hint", but now that I found this thread, I'll try to post it here.
For some reason, I end up with a ton of "duplicate" tracks in my iTunes library and playlists. By this I mean that more than one track in iTunes maps to a single file on my hard drive. (I may get into this problem because I sync my files between my Mac and my PC, and an ID3 tag change made on my PC may cause iTunes on the Mac to think it's a whole new track when I re-drop the files back into iTunes.)
Anyway, Doug Adams has some great Applescripts available to find and/or delete "dupes", but they don't always work for me.
So, I wrote a Perl script to parse the "Song List" which can be exported from iTunes (in the File menu). There are 25 different "fields" associated with every track in the list, and the Perl script allows you to easily pick which fields you want (by editing the Perl script where documented).
Here's the script:
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