About a week into owning my very own 40Gig Ipod (thanks to a generous if frequently annoying reader) and so far I'm fairly impressed. The sound quality with headphones is for some reason less than is desired (and worse than my flash mp3 player), as many critics have said -- though, piped into my fairly crappy stereo system via the dock the quality seems better. ITunes is overall pretty good software -- the autosync is a nice feature and unlike other such programs it doesn't seem to try to take over your entire system when you install/run it.
The clickwheel interface and menu system deserves the kudos it's gotten. Haven't had it long enough to know if some of my nitpicky interface complaints are just a result of my lack of familiarity.