iCloud music will not sync playlist songs

I have searched thoroughly and not found anyone with a problem exactly like this one. I just signed up for a free trial of Apple Music, and turned on the iCloud Music Library in order to access the downloaded songs on my Mac and iPhone 6. (I have never before used iCloud, and have synced my phone with my Mac using a lightning cable.) All of my (quite large) library uploaded to the Cloud, except the songs that were in playlists I had created. These songs now show greyed out on both devices, with the dotted cloud next to them on my Mac, and cannot be played ("Item not available" message on the iPhone). The rest of the albums the songs came from are okay, just not those particular songs that were also in a playlist. I have tried turning the iCloud library off and back on again (on both devices -- several times -- each time waiting hours for the spinny circle to indicate that the uploading had finished), clicking file> library> update icloud music library, and deleting the playlists (but not removing the songs). The missing files are from ripped CDs, so I cannot simply re-download them from the Store, and I certainly don't want to spend hours re-ripping dozens of CDs for 100 or so lost songs. Any useful suggestions would be greatly appreciated!