So for the first time since I've own a Mac with iTunes the whole experience of putting my Music Library back has been a disaster. I had to bring my MacBook Pro in for repairs. Because of a f*** up on Apple's part with Touch ID they ended up replacing the whole logic board with SSD.
After setting up macOS Catalina I put back my Music library folder I keep on an external - Mac formatted - drive to my MacBook Pro.
Frist option: Music failed to load all album art. Loging in with my Apple ID and fetching album art Music did nothing to fix this. Not a single match was made, no album art downloaded. Tried this a couple of times. No dice.
Second option with a clean library folder: Enabled iTunes Match, tried downloading songs from the cloud. One download error after another. Apparently Music was unable to fetch my music from the cloud due to server errors on Apple's side of things. Great. Tracks that did download managed to produce album art though. Also tried this a couple of times. The many download errors made it pointless to continue.
Third option with a clean library folder: used the import setting to get the song files from my Music Library folder on the external drive. Managed to produce imported songs with album art. For the most part that is. All purchased songs from the iTunes Store came up blank. Telling Music to fetch album art once again didn't do anything to fix this issue. Since this option managed to produce the most songs with album art I ended up added the album art myself. I had to manually download each art file from
https://bendodson.com/projects/itunes-artwork-finder/. Unbelievable.
Honestly, what is up? I've
never ever had this much problems with restoring my Music Library from my external drive. With iTunes it was always a matter of placing the iTunes Library folder back to ~/Music and launch the app. Easy peasy.