I have somewhat of a similar problem. Back in Jan, 2016, I downloaded some HD song files from HDTracks, and imported them into iTunes on my iMac. Originally they would not sync with my iPhone 6s Plus or iPad Pro, and I would get an error message for all songs, every time it tried to sync. I know that, back in Jan, 2016, I changed some setting on the iPhone and iPad...for the life of me I don't remember, but, it was something to do with iTunes, Music, or iCloud, and...it started to sync, and I played most of the songs on both devices.
Fast forward to April, 2016, when all the OS X, iOS, and iTunes updates came out...after I upgraded, they stopped synching. I poked around in the iPhone and iPad settings, I I don't seem to be able to find anything to change--in fact, I'm not even sure the item I changed is still there, but...not sure. I've Googled, and read and posted in the Forums, but, No Joy. Since, I know they worked before, and I have the same HW, just updated SW...am hoping that I can make it work again.
Any ideas?
Thanks!