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From what I've read, the PSPGo offers no real advantage if you already have a PSP so I would just go with the iPod.

Also, pretty much what SuperChunk said about the headphones.

-edit-

axumblade said:
I'm assuming you have a PS3. one cool feature of the PSP is that you can synch up your bluetooth headset AND dualshock 3 controllers with teh PSP Go and use them in them.

I've seen a few people mention this and I have a question for you-- where do you put the PSP while you're using the DS3?