Although I have owned an iPod, I have never purchased music from iTunes before. I have transferred MP3 Music files to my iPod with the iTunes program back in the day, but I am not aware how iTunes really keeps track of the music cus I mainly use Google Play Music for my music. Google Play Music lets me upload an Album or individual songs I already owned onto the cloud on my account. From there, all my devices have access to the music files they can download them or not if I choose to do so, Does apple iTunes upload your personal music files you ripped to the cloud? if so its just a matter of re-downloading them again, no?