I don't know if I ever used iTunes to rip music but I did buy an iPod in 2005 so I used iTunes for that for a while. I ran into a bug with it though where it would fuck up the song database on my iPod and half the songs showed up on the iPod as unknown, everything was fine in iTunes. Found out pretty quickly after I discovered that that Winamp could handle loading music into an iPod and never had the problem again.