Hi, I was browsing via google and I saw the thread regarding the iPod and would share my experience with it. The iPod uses a harddrive that will cache about 20 minutes of songs, any sort of hard running or physical activity can cause it to not respond and eventually restart, this is one of the main problems when running with an mp3 based hardrive player. I own a 1st gen 20 gig iPod and have purchased two different cases for it, one specifically for running which utilizes an armband. The iPod will work for a certain amount of time, but it will usually crash within 10 minutes 70% of the time, unless I am doing an extremely slow jog. The iPod mini on the other hand has a different type of harddrive, I don't recall the name, that allows it to endure harder physical activity without it crashing, although it is still not perfect and won't compare to a non-harddrive based mp3 player (something that uses a compactflash or media card for example), it is still "ok" for running. It may or may not crash depending on exactly where you place the ipod (how much vibration it will receive) and the type of case you have. If you are looking for a no fail player, I'd recommend purchasing a nike mp3 player, you can probably find a 256kb one for about 80 bucks (amazon). You could always purchase an iPod mini, which is much more expensive (around 225), but it still may crash when running. If I had the chance to take back my 1g 20gig iPod (I paid 600 bucks for it 2 years ago), I would buy a mini, but with money constraints, the nike mp3 player is my best bet.
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