Does anyone know how I can transfer songs from my old Dell Digital Jukebox to iTunes so I can sync them to my nano?

I have a new Windows 8.1 pc, and a new iPod nano 7th gen. How do I upload songs from my old Dell Digital Jukebox (yes, I know it's a dinosaur, but it still works great) to iTunes so I can sync those songs over to the nano?

Also, I should mention that I spoke to an Apple rep. He sent me a link to download a driver for the Jukebox once we found out that the pc did not recognize the device when I plugged it into the USB port. He told me that once I upload the driver, it will recognize it and I can just copy and paste the songs into a folder, then import them to iTunes. So far it has not worked and when I tried to call back, it looks like morning is the soonest I can speak to someone. So I'm trying on here.

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