Based on my own experience, the PSP will do him until the PS3 (or PS4, or whatever) comes out. Our 11-year-old started out with a Gameboy and slowly 'graduated' through a PS1 to a ('chipped') PS2. But his younger (7 & 9-yr-old) siblings are still getting great mileage out of his 5-year-old GameBoy and accumulated games. The day one of them breaks/loses/swallows it, it'll have served way beyond the call of duty...I would push for the PSP as it is portable but is also a powerful console and it would do him until he is in his teens.
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