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IMO i dont think the PSP2 will fail as the PSP didnt fail (it just wasnt close to its competitor lol).  I doubt the PSP2 should be more expensive than the $299 3DS as its not really adding anything completely new to the handheld world unlike 3D but seems to just buff it up from the original PSP.

A reason i could see it fail tho is because its completely digital.  Mainly because having some kind of cartridge or disc makes it alot easier to use/buy for kids and parents.  Parents hate to buy things they do not understand how to use and a lot of parents these days still do not know how to download the simplest things online.  Unless the parents just buys it, hands it to their 6yr old kid and say "here you go, you figure this out".  Of course some kids are tech smart really young but not all.