I never bought anything because it was "old" or "nostalgic". Every equipment I have bought in my life was "brand new" and "state of the art" at its time. We just grew old together with some of them. I recently coughed a lot of money for a "state of the art" home theater system for the family. Lots of big speakers and mean looking black machines outputting superb sound. I really am amazed by the clarity and depth... The now "old" stuff which grew up with me are in my study and in my office at work. When I listen to them, I listen to my old friends. ?nexplicable feeling...
You should listen to the ipod then - point is that most new gear objective might not not have been better sound, but better looks and convenience. That's where the progress was.