To manage music on your iPod, you will need to use iTunes (even on a Windows PC). Use the "sync" feature to only sync "checked" songs, as unchecked songs in the music library can be removed. Make sure there are copies of each of your music files on your computer. In the library. you can sort tracks by artist, album, and custom playlists. If you uncheck all, then you can basically clear your iPod of space and then pick what you want to add anew.