I finally caved and bought a Sony PSP a few days ago. I'm sure no one is surprised that I picked up one of these (have you seen it?!?), but I'm sure some (including me) are surprised that I held out so long.
Within minutes I had it booted up, connected to my wireless LAN, and downloading a firmware update. Shortly after installing the v1.52 firmware I remembered reading that the Japanese v2.0 firmware was floating around and that this version included a web browser (not the Wipeout Pure hack) and worked fine on "English" machines. Not wanting to buy yet another cable (you can't move files from your computer to the PSP over Wi-Fi, though after the v2.0 update I'm assuming that you can probably download files through the browser), I couldn't come up with a reason why the USB cable that came with my Canon 20D wouldn't do the trick, so I tried it out and it worked flawlessly. After transferring the update to the PSP over USB and then rebooting, I was quickly browsing my site on the device. Unfortunately, v2.0 has not been "cracked" yet and so any emulators or other things I want to run will have to wait, but I'm sure it won't be too long before the deed is done.
Playing games and hacking away at this thing will be the death of me. It's not without reason that I've denied myself a gaming system for the past few years (save the Gameboy Advance SP).