I've had mine since the day they came out and I'm happy with it. Since most of the good reasons to get one are posted above I'll focus on the negative:
The web browser is worthless: The PSP lacks the ram to handle most sites and the browser usually crashes or gives you the annoying message that "it lacks the memory" to display the page properly. If you visit sites with lots of text and very little pictures or video then it won't bother you much but you should be aware that most modern cellphones offer a better web experience.
As an MP3 player the psp is disappointing: While the quality of the audio is decent enough, the volume doesn't go up high enough and the 5 or so sound presets are just plain laughable. While you can set up playlists fairly easily and putting music onto the memory stick is just as painless, the psp only registers files that are one directory deep meaning that you'll have to individualy list every album in it's own folder......with mp3 players that make finding and organizing your music the exact way you want it - Sony should have stepped it up.
The included earbuds suck: They're uncomfortable, do little to block outside noise and aren't loud enough.
Memory is expensive: When I got my 2 gig stick for Christmas last year it cost my g/f about $160 (Sony brand) and while the prices have dropped - you can get a 4 gig for about the same $160, you could always pay $60 more and get a 30 gig Ipod.
There are very few good games: Most of the games available are either sloppy port jobs by lazy game makers or are just terrible. Homebrew is definetly the way to go but as stated above, you can't upgrade to play homebrew games and that eliminates the ability to play newer games.
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It's a great game system and a good value for all that it does but you shouldn't it expect it to be the mobile entertainment solution it's marketed as. In fact, full-time use of anything other than it's gaming capabilities will lead to a bit of frustration.
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