Songs no longer sync to my iPhone 5s

[breggsy]

I've had my playlist of local files that are on my laptop downloaded and available offline for over a month now and when I accidentally switched Available Offline to the OFF side earlier today all the songs were removed. I didn't panic and turned it back ON again, but now I am panicking because nothing is redownloading even though I am connected to the same Wi-Fi as my laptop. All I see is "Waiting to download." at the top of the screen. I tried downloading a different playlist and that worked FINE but whenever I try and download a song from that local files section on my laptop it fails.

Please help fix DX

[breggsy]

Removed my iPhone 5s from my list of Offline Devices and now I have no idea how to get it back on the list so I can redownload these playlists... SOMEONE HELP PLEASE

[breggsy]

89 Songs, over 4.0 GB left on my phone, what's up???