So the latest update.
I took all the files, named and tagged them to my liking, and put them into the main folder of the USB, using Windows (I guess I had never tried this exact combination) and it worked.
3315 files all read, tagged, most have cover art, some don't for some unknown reason (i'm guessing sizing issues)
Anyways, thanks for the help. I still may do the iTunes thing on an SD card if the cover art becomes a major eyesore.
D