I took the plunge and started up Apple Music and iCloud Music Library on my main machine (an iMac) without understanding the whole "your ripped music on all your devices, but now with DRM" issue. Now my MacBook (which previously had an empty iTunes Library) has my entire iMac library, but with DRM. If I had subscribed to iTunes Match prior to this my understanding is that I could also have my entire Library on the MacBook, and without DRM. I have Time Machine backups that I could use to revert my entire iTunes Library back to prior to June 30th, but what would happen if I subscribed to iTunes Match right now? Is iTunes smart enough to remember which songs were originally ripped and replace the DRM versions with iTunes Match versions on my MacBook?