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I used an original iPod in 2024, and it was pretty fun
(www.spacebar.news)
This is a most excellent place for technology news and articles.
I still use my iPod Classic. I can plug it into my car for when I'm out of FM range, and I have a Bluetooth adapter for it that plugs into the headphone socket & lets me listen via my hearing aids. It's better than a phone for me, because the mobile signal is weak where I live, and most of my garden is out of WiFi range. It fits all my music and still has room for podcasts.
iTunes sucks though, ugh.
Check out Rockbox
You don't need the Rockbox OS on your iPod to use their sync tool, if I remember right. But it's a better experience in my opinion.
Also, you can uograde your iPod with more storage, more battery, and Bluetooth.