The number of times that the iTunes library file has corrupted on my iMac is insane! I have a very large iTunes library. It consists of all the CDs, LPs, Cassette Tapes, and even some Reel-to-reels that I own, and have converted to digital. The library is about 23,000 songs and well over a thousand albums. With a library of this size, I have to have it stored on an external NAS, because I also have over a 1,000 TVs episodes and movies too. My NAS is a Drobo5N with 18TB of storage on it.

Here’s the issues that come up periodically in iTunes, and everyone of them drives me totally nuts.

• First, iTunes has never really done a good job of supporting NAS drives (or really any external drive, as I had these same issues when I had an Drobo directly attached to the iMac).
• Second, every so often, iTunes loses track of where a song is. This is shown by a small (i) symbol next to the item. If I try to play an album with songs with this symbol it will skip those songs. If I go in and double click on the song title, iTunes magically remembers the location and the song will play.
• Third, duplicate songs. If you ever go in and tell iTunes to consolidate your library, it will kindly duplicate the songs into it’s own file hierarchy, leaving the original there to. This makes sense from a safety perspective (not deleting the originals, BUT it will then (at times) add the duplicates back in. I think this is a legacy issue when you tell iTunes to monitor a directory.
• Forth, album art. I have spent a TON of time making sure that all of my album art actually matches the Albums I have. So if I converted an LP to iTunes, I take pictures of the LP so that I can match it up. The number of times that I’ve loaded my library only to see the Gray background with the Musical notes in the picture instead of my nice Album art is beyond count. I have used Doug’s wonderful scripts to actually put the album art into the songs, but since iTunes loses track of some of the songs, it doesn’t always work.
• And finally, Meta Data. I like to sort my albums in a very specific way. To that end, I have changes sort artist, sort album, etc. but it doesn’t seem to stick there either.

I have been using the iTunes Match service (which I love!) so that I can have my music library on all my devices when I travel, so I would really appreciate it if Apple would spend SOME time and actually fix bugs in iTunes, instead of tweaking the UI.