I wasn't really looking for an iPod... just an MP3 player.
My 60gb iPod (not video) was $320. As far as I could find there were no competitive mp3 players at that price at the time. The closest match at $350 had 30gb storage & the interface was a pain.
I find iTunes software to be fine on PC, its just the iTunes music store that I can't stand (as its virtually impossible to transfer the songs purchased onto a CD). I get around that by not buying anything from iTunes. Its always cheaper to buy actual CDs from amazon or ebay