I've got some Sony usb-stick type thing which does me fine, rarely need it but it's 4Gb of music with a battery that lasts a silly long time that 'just works' (with the exception of drag and drop on XP without installing drivers iirc, because they just have to try to be clever don't they)
I did have a 16Gb iPod Nano a while ago, I was looking for a setup for my car/portable music, read around a lot and actually decided on a Sony alternative that was cheaper and supposedly better sound quality, plus had the added benefit of drag-and-drop media management, however no head-units supported it explicitly so I went with the iPod, my experience wasn't so great really:
User error I agree but it seems that Apple decided to mess around with the charging pin so the head unit no longer charged the iPod, useful.
Battery life was ok but nothing more, meaning mostly daily I'd need to take the ipod out of the car to recharge it.
Sound quality, oddly, wasn't that great through the head unit, at the end I replaced it with a USB stick which was far better sound quality (decent amp'ed speakers)
And of course iTunes, an utterly awful piece of software, bloated with features I had no desire to use.
So yeah, I replaced the ~£120 16Gb iPod with a 16Gb tiny USB memory stick for the car and the 4Gb Sony thing for portable-ness (it's rare I need that), total cost was half the price of the iPod and served my needs far far better.
Recently I've also got onto the google music beta, so through my phone I can play any of the >5000 songs I own whenever I want, I doubt I'll ever buy an iPod again as it's simple not needed
