iTunes is the work of the devil, but there are some programs out there that will work with music that has been 'diddled' by the iTunes software, allowing you to play it on a non-Crapple device. Personally speaking, I just use windows media player library for organizing my music, for the most part it's easy to work with & doesn't do anything funny regards DRM that might otherwise prevent you playing music on a separate device. Just drag & drop files onto the connected device, and away you go
