Great OP. I'm an Apple guy, so I never had a Zune. I do remember Microsoft getting a lot of flak about the brown Zune, I still think it looks great! I wonder what one would cost now...
Oldest thing I'm still using is probably my car stereo. It's a 2003 Subaru with a tape deck and CD changer. The reason I keep it, is it also has a weather radio (good luck finding that in a new system!). I also have a cassette to 3.5 adapter that goes into a bluetooth adapter. I get the best of new and old, it works great!