I finally figured out how to do what I wanted (with regards to finding songs that do not have files). Here is a step by step instruction guide (mostly so that the next time I run in to this problem I won’t have to “reinvent the wheel.”)
- Create a normal (non-smart or manual playlist) play list (CTRL-N), name it “M-All Songs” (that’s short on my playlist naming convention for “management playlist – All Songs”, I normally don’t play the management playlists, they’re just used for managing my iTunes library.)
- Go to “Music” and select all (CTRL-A) music, now drag these songs in to the manual playlist you created above (M-All Songs). Note: Due to a quirk in the way that iTunes is programmed, iTunes will not permit you to drag songs missing files in to a manual playlist. Imagine that.
- Create a smart playlist (CTRL-ALT-N), name it “M-All songs missing files.” Configure the smart playlist as follows:
- Check “Match” all “of the following rules:”, and set the drop down to “all.”
- “Playlist” is not “M-All Songs”
- “Genre” is not “Podcast”, this will remove podcasts which might show up here. If you are like me, you uncheck the podcasts you wish to keep rather than deleting them so that they will not be copied to your iPod. This will make sure that you’re not shown any podcast entries that are unchecked (since they would not have been copied in to M-All Songs). Alternately, you can just check “Match only checked items.”
- Check “Live updating”
- Go to your new smart playlist “M-All songs missing files” and find the files or delete as required.
Keywords: iTunes, find duplicate files, delete duplicate files, iTunes playlists, delete missing files without plugin.
Keywords provided in case someone decides to google for the solution to the same problem I was having. Hopefully my page will be found and help some other poor shmo who was suckered in to buying an Apple product. (BTW Apple, you suck. At least Microsoft would have provided me a way of backing up my database without needing 12 DVDR disks to backup the entire bloody music library just to get the configuration data.)

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