iTunes Match working on iPhone but not 2nd Mac

I have iTunes Match with one computer (Mac Mini) set as the master and holding all the physical music. While I can play everything fine on my phone, my Macbook Pro only plays some music while other tracks say it cannot locate the files and won't play. Strangely, the songs it does allow to play seem to all be in one of my playlists. This used to work fine up until maybe a few weeks ago, possibly when the Mini was upgraded to Golden Gate while my Macbook is stuck on Tahoe. I've confirmed that Sync Libraries is on, I've deauthorized and reauthorized the computer and still can't get all my songs to play. Since I can hear everything on my phone, I suspect the issue is in the Macbook Pro and not the host computer. Any ideas?