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In my opinion it comes down to hand size. If you have large hands like me, then the PSP (especially the 1000) will feel extremely comfortable while the DS and PSP 2000 are very uncomfortable. On the flip-side if you have smaller hands, you'll probably like the DS or PSP 2000 as the PSP 1000 might be too big and heavy.

All handhelds will cause cramping, as they are made for portability and thus have cramped controls. If you can get away with not using the Nub on the PSP or the Touch Screen on the DS, then they have similar controls and playability. Personally I find the DS a pain in the ass to play, and have dropped more styluses in the toilet than I'd like to admit.