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Long time ago, I put all my CDs and a lot vinyl into iTunes. About six months ago, I noticed tracks that should have been there, weren't. Yesterday, I had a closer look. For multi volume CDs, the first 16 tracks of CD 1 are gone. For single volume CDs, track one is gone. In all, about 3,000 tracks are missing.

I suppose it's theoretically possible I deleted them, but it's difficult to see how I would have done this.

Is anyone using something other than iTunes to organize songs in digital form? Not sure I trust it anymore.

Are you just looking at the listing in iTunes, or the folder where things are kept?

There are options that have to do with "keeping the iTunes folder organized" etc. You may have to do some searching.

Hope you find em. I've know iTunes to forget whats on a drive, but have had it delete anything.

A lot of folks have pitched their CDs and other media. There's a big lesson in your experience. Backup in multiple medias. I've never met a HD I've trusted!

There are so many ways to view tracks in iTunes. How are you doing it? Albums or Songs? Regular or Classic views? You could try to reset the library (Preferences). Is the Media Folder organized option ticked?

Things can get misplaced. I have a lot more than 3,000 tunes but have never lost one.

Since path corruption often happens after High Sierra installs, the first thing I would do is a Safe Boot.

Multi-volume CD organization is a clue to the problem. Every time I enter one I have to specify how many volumes and where a tune fits in. I often have to reboot for iTunes to the display it how I entered them.

I always use the Song view with Artist and Album lists above the song list. What's showing in iTunes is consistent with the files in the iTunes folders on the drive. I recreated the iTunes library by starting a new library and dragging all the media folders into it, but that didn't fix things. Just got the same thing again.

On multivolume structure, I usually edit the CD Info panel when importing. The suggestions iTunes makes cannot be trusted. In any case, it is not likely that this is the cause -- everything was properly labelled and accounted for on the initial import, and was for a few years. Perhaps it happened with one of the OS X or iTunes updates.

I have all the original CDs and can get a lot from backups, but it's still a PITA doing this stuff. Maybe the thing to do it to get a good metadata editors, leave it all in the Finder, and use a different player.

I'm wondering if the same database software is used for Photos and Aperture.