Q: Problem syncing to Iphone 6

I just bought a song off Itunes store on my phone, went to my Win 10 computer, saw that it showed up in my purchases, added it to a couple of playlists and sat back as it synced. When I looked at the playlist afterward, disconnected from computer or connected, it was not there. Resynced with same result. Looked at the phone under devices while hooked to computer and there it was, in both playlists and purchases. Unplugged the phone and it's not there anywhere. Tried restarting the phone, all is up to date. Any ideas on what to do?

While I have you here, I noticed awhile back that after connecting the phone to my computer and looking at a playlist under device that a few songs were greyed out with a broken circle on the far left. If I go into info and look at the status it says Waiting. Waiting for what? Those songs, unlike the one above, show in my playlists and play just fine. Waiting for the second coming maybe?

I have been using Itunes since it came out for Windows with no real problems other than operator error, but lately (since Itunes 11 update) it has not for me as far as features and technically it has not been as up to snuff. I spend a LOT more time looking here and elsewhere for issue solutions.

Thanks for helping!