Cannot sync music in iTunes

I am unable to sync music playlists over iTunes 12.3.0.44 to my iPhone 6s+ on 9.0.2.

I have tried the options both checked an unchecked for Sync only checked songs and videos and Manually manage music and videos. Each attempt displays that some amount of space will be allocated to audio on the phone at the bottom of the screen next to the sync button. But once I start the syncing process, it fails to load any music at all and then it shows that no space has been allocated for audio.

I have previously used Apple Music but have since canceled it. I currently use iTunes Match, but that also fails to display any music that I have uploaded on the phone. It has been disabled on the phone in an attempt to sync w/ iTunes.

I have attempted rebooting both the phone and iTunes and also restored the phone from iCloud backup. Nothing has worked so far.