iTunes & Music sync issues

Ok, so I turned off iTunes Match, so I can have the songs on my iPhone.

Upon turning off iTunes Match on the phone and in iTunes, I went and told iTunes to sync my music.
Here is how it's setup

Sync Music

• Selected playlists

• Picked my playlist (Music)

Hit Sync.

My 'Music' playlist has around 160 songs.

After I synced my iPhone, it only synced 78 of the 160 songs.

After looking at the 'Music' tab in the iPhone, within iTunes, it shows this.
I don't know what the little icon on the left means, next to the check mark, I'm a little stumped on this one.

 

I've done the above mentioned.

For some reason it doesn't want to sync those, but when I hooked up my iPod, and it synced all the songs, so I dunno.