Minor nit: The Archos mp3 players required no desktop software at all, they appeared as a USB mass storage device and you could just copy your files over - for me still the preferred way over any other "music sync" solution...
But of course, in "corporate" they are going to require a "user friendly solution"
It (was) usually a VB program done by people with no UX talent, on a budget an a short timeframe and with no testing as well. Also they make file copies take magically 3x as much time than copying using Windows explorer.
Not to mention iTunes is a better solution, because it's your music library integrated with syncing. It's different for example than having one program to sync and another to listen. (Similar solutions like Amarok + iPod plugin work great as well)
