Well I think I may have figured it out:
I reformated to NTSF.
Instead of dragging my itunes music folder, I clicked into the music folder and moved all of the folders with the listed artist.
It used to be:
Music/Itunes/Itunes media/Music - and I would drag that music folder to USB.
But now I clicked into music folder and selected all of the artist and moved to USB.
It took just a few minutes to index everything - and all of the music seemed to have appeared and have been read by uconnect.