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I've never played with a PSP.
However, the miss'us got me a 60gb IPOD for Xmas and I take it with me everywhere.
It syncs with Outlook calendar and appointments, I can store my contacts on it as Vcards, can view text files on it, etc. It's actually a pretty handy little device. That and the 60gb allows me to not need to carry my Laptop everywhere - can use the Ipod as a go-between for home and work for data storage.
However, I fucking HATE Itunes as a piece of software and the Ipod's music organizing capabilities / issues.
BTW -- how big is a PSP compared to a 5th gen Ipod? I'd have to say if there's a relative size difference, then the Ipod would definitely be favorites in more of portability.
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