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I had a number of Sony digital music players like the NM-MS10: https://en.wikipedia.org/wiki/File:NW-MS10.jpg

Their main drawbacks you're required to convert all the MP3 into Atrac3 using their atrocious software. It is hard to imagine now, but iTunes was a few generations ahead of anything else in speed and ease of use.

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They were a few generations ahead of other extremely locked down devises. They were terrible when compared to devices that just allowed you to copy files to them.

I used MP3 feature phones before I got an iPod and the music library system of the iPod was miles ahead of manually managing my music. Having new songs and album art automatically sync onto the iPod, having play counts sync back, having smart playlists update, it all exposed what a garbage system manual file management was and made me yearn for the future we were promised with the meta-data driven file system of BeOS

Yeah gonna have to disagree strongly with that. iTunes abstracted away the need to manually manage music files. Very few non-nerds actually wanted to do that.

Jamming iPhone-related features into iTunes bloated it up, but in the beginning iTunes was a pretty great piece of media-management software.

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