My top choice is Sony, but iPod isn't too bad either. iPod has to be doing something right if they're so popular, right?
I prefer Sony's interface over the iPod. The one thing that really got me with the Sony is the battery life. Now, my Sony is a bit older and things may have changed with recent versions, but Sony's battery life is immensely superior to my ipod. 80 hours of playtime for Sony vs. not quite that much for the iPod. I used to walk four blocks to work from where I parked so I used my Sony while I walked to work. I got to listen to a song or two, then I'd plug it into some speakers at work and listen for part of the day. I didn't charge the Sony for about three weeks. I tried it with my iPod and I had to charge it after 4 days.
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