Hi Brad.

If I remember rightly your using supernova? With supernova you might need to make sure that Supernova is using the correct map file, sinse Itunes is one occasion where you can't get by with the default map and need the specific Itunes one.

It's fairly easy to do, once you've got Itunes running, go to the supernova control pannel and to the file menu, new and then select new map, find the Itunes map in the list and vuala!

I've had to do this with several versions of Itunes eleven, sinse though the map was the same supernova's only went up to version 10 and needed setting manually for the later Itunes versions, though I notice sn now has a version eleven map specifically so that should be fixed.

It's funny sinse usually with supernova you don't need to worry about map files at all and can get on with the default, I blaime it on the stupid screen layout of Itunes with it's silly trees and elements chucked all over the place that you can't really do anything about.

I'm hoping that the ability to do direct file transfer in Ios 8 will mean I don't have to use Itunes to transfer books and music onto my phone, and can just copy the folders over the way I would with any ordinary mp3 player, but we'll have to see.

but you can transfer your music by just copying it to my music\iTunes\automatically add to titunes media. I hope I remember the path of the folder correctly.
so you can go into this folder and paste any song you want and if sincing of music is set to automatic the songs will be copied to your phone.