The problem that Apple never saw fit to comment on – the terrible playback stutter has now disappeared. Whether it’s due to my total removal of iTunes 7.6 (in anger!) and thus a clean install of 7.7, or if Apple has in fact fixed something, I don’t know. Maybe it’s simply because I removed DRM from all my AAC files to play them through Winamp?
Nevertheless, it means that I’m back to iTunes for now. I used Winamp for a while, but sadly Winamp has become pretty bloated and its interface is… well it’s not iTunes’. Besides, Winamps built in iPod-support didn’t do it for me.