I’ve got a huge amount of music in my High Sierra iMac iTunes app, roughly 60GB worth and it’s a mess.
It’s nearly all CDs we ripped long ago and then I added them into iTunes when our music server died but it’s been 10+ years so I don’t even remember how I did it. But there are lots of other sources in there too.
There is the folder Music at the top level in Documents. Within the Music folder there is a mix of loose tracks, and a folder named iTunes. Then within that iTunes folder there is a mix of loose tracks, folders with the artist name, some with the names spelled incorrectly and there is also a folder called “iTunes Music” that appears to be similar to the outside folder structure in the iTunes folder but it’s missing some of the individual tracks in the enclosed folders. Some of the tracks have no artist or track name because they are from local artists who gave them out as demos during live performances at the Pub and not standard CDs. I’ve got duplicate songs but by different artists that I still want. I’ve got duplicate songs but from different albums by the same artist (think original vinyl I digitized, then also bought a remastered CD and sometimes one or more live performances) and I want to keep those variations. I’ve got a spoken history from my Uncle from WWII when he was in a POW camp and other similar odd bits and bobs of sound files. And of course I’ve got music I bought from Amazon, mostly individual tracks although I did buy some albums and a few from Apple as well.
I’d like to clean it all up, with a nice neat folder structure for each artist and then the albums as separate folders within that and then the tracks with titles in each album folder.
Now I can go in and using finder clean it all out by moving tracks into folders by artist and then by album and renaming them as needed. It will be slow but doable. I’m concerned as to how iTunes will handle that and then, more importantly, how best to move the whole structure and data so that I can do a nuke and pave and upgrade my iMac to Catalina before moving it all back onto a nice neat and clean system. I do have my new MacAir running Catalina that has an empty Music folder with nothing in the Media folder that I could use to dump stuff into once it’s clean if that’s an option.
Any suggestions, warnings, or other tools to help me clean that all up would be appreciated.
And for the record, using iCloud to synch is not an option, I want to do it all in house and I do not use iCloud at all and I’m not planning on starting.
