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Might be worth trying Linux players built with libgpod, as listed on the Arch wiki.

Apple is still updating iTunes for Windows. You could certainly run it in a VM if you wanted to.

iPod batteries are readily available on ebay and AliExpress. You can also replace the Hard drive with MicroSD cards using this adapter.

Have you actually tried to run iTunes on windows? It's like a nightmare that never stops.

I see people saying this a lot but in my limited experience, while iTunes for Windows is less than great it’s never been that much trouble.

Yes I am running iTunes on Windows and it works just fine. What issues do you have?

I wonder if Floola still works? It was great for managing iPods on Linux back in the day.

Have you tried Rockbox?

- rockbox.org