I had an MP3 player before the iPod as well. It was a 64MB Rio and it held ~10 songs.

The thing was iTunes wasn't designed to be a music loader, it's a music manager. This became evident when they introduced smart playlists.

A few of my friends had Nomads, they were large, heavy and the UI was archaic in comparison.

Back in the day you install iTunes, stick a cd in your computer, iTunes recognizes the cd, rips it, names the tracks, loads it onto your iPod.

This is back when you had to figure out which Mp3 encoder you wanted to use.