As a long time gamer, I've always been amused by the portable consoles. As a kid, I always wanted the Sega Game Gear, the Nintendo Game Boy. They were all amusing, heck every kid wanted them. Now, as an adult, I finally get to waste money on the PSP.
Playing it is pretty fun, I'll admit that. The screen is very nice. The range of accessories is decent. The game selection is fairly good. The ability to play via WiFi is priceless in my opinion. The PSP does have some major downfalls though, mainly the UMD format. UMD really crashed and burned, and the PSP community knows this. I guess it was Sony's attempt to thwart PSP piracy, but obviously that didn't go to well due to the memory stick opening a whole realm for people to do that. So in the end, they got the piracy and a dead format.
To top on to the negativity, which I really am not a negative person but this stuff must be said, the PSP is not really all that portable. It's a large item. The nintendo DS is something you can stuff in your pocket and go around with. The PSP is like a little briefcase though. It would look quite awkward in your pocket unless you have some monstrous cargo pants are a huge utility jacket. Lastly, battery life could've used a bit of help too. Overall, I wouldn't buy the PSP again, it lost it's entertainment value pretty fast for me, and judging by the amount of them on ebay, many agree.