Clean up iTunes Music before Catalina Upgrade?

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.

There are a few options to help organize things in Catalina’s Music. I don’t remember if these are available in previous versions or not. It looks like these options would do a lot of work toward organizing and consolidating your library.

In Preferences:

In File | Library | Organize Library…

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I just tried that with 2 albums from an artist that has the name set incorrectly in iTunes.

Moved 2 folders corresponding to albums from same artist but misspelled name to desktop of Catalina machine
Opened Music app and set preferences
Imported those folders
Comes into Music into 2 folders with wrong spelling of name propagated to the Music app.
Also lost the Genre metadata I had added in iTunes.

So maybe I’m missing something obvious here but that doesn’t seem like it will clean up anything.

Sure, it isn’t a panacea. In reading your OP, it seems you have files scattered to the four corners of your hard drive, with varying folder structure. The options shown above should help with that.

The app that I used to use for this was SongGenie (see Macworld review) but it is apparently now discontinued.

I’m not sure if there’s another app besides iTunes for this now.

Actually, now that I think if it, MusicBrainz Picard might be an option. I haven’t used that in ages, but I believe Merlin Mann has mentioned it as a tool he uses too.

Yes and no, the files are all in iTunes in the folder structure it created when I initially imported stuff but it’s been through 3 machines and lots of operating system revs since then. It appears there are duplicates (file names the same) but I don’t see true duplicates in iTunes when I look at songs by name. (comparing track times etc.) I’ve done some bouts of cleaning up metadata to try to fix the artist name differences which appear to be at least partially from uTunes having multiple versions of people when it goes out to search for artwork but never really finished it. I only got the worst cases done. That didn’t clean up the underlying file names or locations, something I actually kinda thought was happening when I clean names etc. up in iTunes.