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You should wait until after e3 because Sony is probably going to give details about their next portable to compete with nintendo's recent 3ds announcement. Remember that the ds and psp released close together so that will probably be the case with the next iterations of the portables.

Also e3 is usually a place where price drops are announced so you should wait just to see sony is going to reduce the price first. I would recommend that you buy a psp 3000 or 2000 and pass on the psp go. You won't have a problem finding game umd's but a lot of games still haven't been released digitally yet. The psp 3000 or 2000 gives you the choice to get games either way.

Meanwhile with the psp go you are stuck with digital releases only.