Pardon my ignorance, but how does one tell the difference between the iPod Video 5G and the iPod Video 5.5G?
In nearly every test I've done with my iPod Video 5_G, my songs sound richer and more lively than with the Clip Zip with a 32-ohm headphone. The soundstage is also larger both in terms of depth and width.
I've heard that the Clip+ sounds warm, but I personally don't hear it especially compared to the Video 5_G. I find it fairly neutral/slightly analytical but the soundstage is quite small; maybe it's just me, I dunno.
I'm going to post in the sound science forums about measurements and soundstage since that seems to be of interest here.
Back on topic, I have no idea how the Classic sounds next to the Clip+ unfortunately. I was considering getting the new Classic though because apparently you can install Rockbox on it even though it's not on Rockbox's official list. I'm having second thoughts though because I don't like the "click wheel" too much and prefer the "old-school" navigation with the Clip Zip's media buttons.