I'm also having alot of trouble hitting those diagonals. As far as making it easier.. I remember there being an attachment you can stick on your D-pad to help with that.
 I've also heard that the newer PSPs that've been manufactured also had raised D-pads for easier diagonals. There's also a mod that involves opening your PSP to stick a piece of paper under the D-pad to raise it that way. That'll void your warranty though.
 Myself, I'm planning on trying the mod. I have a launch-day PSP and since the warranty's been long expired, I'd have nothing to lose.
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