It looks like Sony is releasing a new firmware update to the PSP July 27th that will have a lot really great features- a web browser, h.264 support (for TV watching), wallpaper, image receiving, video navigation updates, mp4 support and a lot more. I wouldn’t be surprised if you couldn’t sync with iTunes soon as odd as that sounds. Any way, this will most certainly break the ability to play homebrew code, so you might want to hold off of get another one. Link.
PSP updates coming july 27th (don’t update, yet)