IMO, as flawed as it may be, iTunes is the best part of the whole iPod ecosystem. The parts I hate most in iTunes are where they've cut and created feature disparity when connecting an iPod (versus not having one connected).

I don't know if this affects you, but you can likely give up on creating playlists on the fly with the iPod. It's sort of possible, but a real PITA since you can't modify the currently playing list of music.

I find that an iPod touch is either suitable for playing through all tracks on randomly or selecting individual albums using Coverflow. With a classic I'd say you're in the same boat, but without Coverflow. In either case you can't change the way things are sorted nor really change anything about what gets display and what doesn't. By contrast iTunes can do just about anything in this regard. I'm not sure who maintains the UI for the iPod, but they clearly haven't been talking to the iTunes guys.