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some work arounds are offered on the sony website, but if you use i-tunes like i do - you have got to make sure you get the itunes plus labeled media.
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my wife has an ipod nano, and while the sound is good, the ipod hs had a reputation for breaking and i found the itunes store a nightmare to navigate.
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i also love the drop and drag feature and not having to mess around with itunes.
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price is great & you are not limited to using itunes.
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1.) if you are looking for a player that you want to use with your itunes library, spend the extra $50 and buy an ipod.
Positives:
Large Capacity, Storage Capacity: 8 GB, Audio Format: WMA (DRM),MP3,WAV,AAC, Number of Songs: 2000