Apple Music Library Doesn't Load

At least 50% of the time the Music app on macOS Catalina doesn't allow me to listen to the music in my Music Library. Whether it is a song, a playlist, or an album, I cannot listen to it. The songs are all greyed out and doing any actions has zero effect. Interestingly, I'm able to go to the "For You" tab, go to my profile, and view my public playlists and listen to them that way but not if I try to access them through my library. This happens the first time I open the Music app, without fail, every time. But once I close the app and reopen the app, it will work most of the time. The only way I know Music will work is if the bottom left of the app window it shows a dialog saying "Updating Cloud Music Library". But in some other cases, I will have to do the reopening steps multiple times (5 - 15 times) for it to finally connect to Apple's servers and load my iCloud Music Library.

I've tried this on multiple MacBook Pro's (13 and 15), different macOS Catalina versions, restarted my laptop, restored to factory settings, unauthorized and reauthorized, everything! I'm fairly certain this is a bug somewhere in the Music app.

Also, Apple Music works on my iPhone while the Music app will not.