I have recently bought a new 8th Gen iPod Classic to replace an old broken iPod, as I am kind of tied to the iPod brand as so much of my stuff is ripped using the Apple codec, and also with 46 gig of music etc on iTunes, other options will be just too much hassle for me. Also, I have no real problem with iTunes, which some people seem to hate, but I find it easy and straight forward to use, and also even plays my 96khz 24BIT wav files.
Anyway, the real dissapointing thing is the volume of the new iPod's, which is simply pitiful, and needs to be almost flat out to be loud enough for me, using UE TF10's and custom tips. Also, I use my iPod mostly in my car, feeding from the headphone into the line-in socket for the stereo, and is so low now I am having to buy a new cable that charges and gives a line out. Luckily I have a FiiO E7 and line out cable for protable listening, and it sounds fantastic IMO, but for listening without an amp, I would avoid this last generation.