Whoah there, iTunes is not ease of use. I had an MP3 player before the iPod was ever relased and it was most definitely easier to load music onto.
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.
This is back when you had to figure out which Mp3 encoder you wanted to use.