Not looking at any new MP3 player personally. I have an old iPod 2G. Don't remember how I got it, though. Was it a gift? Or did I buy it used? I don't know. It made me sad (messed up on high bitrate MP3s and also never officially got gapless playback), until I discovered rockbox. It's always plugged in; I only listen to music when I'm sitting down, so it's working for me. Drag and drop into folders sure beats any additional management software, IMO.
I don't listen to music on-the-go. If I have my tunes playing, I get so caught up in the music I forget where I'm going. Almost gone run over once. Never listened to music while walking again =D. Then again, I consider the noise of the city to be a kind of music, really. Used to think city noises and sights were ugly, but now I try to find beauty in everything even in this rusty, dusty old town or the dust bunnies in my computer.
But let's say this iPod did die. I don't think I would find a replacement. I'd just play music from the computer or something, since I don't take my music anywhere.