I don't know anyone still using MP3s. Everyone has moved on to one streaming service or another.

As a parent, I don't feel like purchasing offline music for my kids as it's one more thing they'll outgrow as they get older. I don't see a need to shelve a thumb drive full of Paw Patrol or whatever next to their outgrown jackets and rain boots.

On Windows the main software is CopyTrans, which even supports modern iPhones! For purely iPods, here is also the jlPod WinAmp plugin that works well

iPod classics go for $200 and up for the later versions, and sometimes thousands of dollars for the earlier versions on eBay.

iPod nano similarly goes for about $180 used.

Hmmm, it looks like I can maybe buy a 5th gen nano for about $60. That may be worth it, if I'm sure I'll always be able to put mp3s on it.

Wow I picked up a working nano from the junk bin at a thrift store for $5, didn't realize that was such a deal