Make sure that your CD player can actually recognize CDRs. While the great majority do, some other models do not. Try the burned copy in a different CD player. Most DVD/CD burners that come with computers are able to do read rip and burn but that might not be the case otherwise.
Moreover, every single Itunes version works a little differently, older versions had a prominent "Burn" icon in the interface, now it is somehow hidden and you have to go to File and chose "Burn playlist to CD" option.
I suspect that your transport does not read the burned CD...remember that when you see the left column option of the Itunes, you are actually choosing to play the burned CD with its proper CD icon rather than the playlist. I do not think this might be a problem but things can get visually blurry with Itunes.