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I bought a US launch PSP back in the day, sold it a few years back to help pay for my 360. Never owned a DS.
As a gaming unit, the DS wins by a landslide. The sheer amount of original content, the high number of good-quality games, plus the homebrew community put together make Nintendo's handheld the obvious winner in this category.
As a multimedia device, the PSP tends to shine a little better. The homebrew community on Sony's handheld is beyond ridiculous, shit out there can transform the damn thing into all sorts of crazy shit, in addition to the fact that emulation is hilariously simple.
..The games however, either are ported from the PS2, or to the PS2, making the video game aspect of the device almost pointless, unless you are really into portable gaming.
The DS has plenty going for it that can only be found on the DS, in addition to many of the same features the PSP has, so it is the more worthwhile handheld when it all comes down to it.
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