Once you installed it, start the VM and plug in your iPod. For VM to see it, on right top there is a … menu, go preferences from there. Switch to Devices & Shares tab. It should see your iPod now, just enable it. Also set a shared directory from below so you can put your music files there before uploading them to your iPod. This is the iTunes version I use: www.filehorse.com/download-itunes-64/35820/