Buy a PSP3000. Seriously, I own two of the 1000 models and I can't stand using them anymore. The screen on the 3000 is infinitely superior. MUCH higher contrast ratio, much faster response time, and superior color reproduction completely change the appearance of all PSP software. Seriously, it's truly a night and day difference here. The LCD refreshes faster than most PC LCDs I've used as of late even, so it's really pretty quick and shames the 1000 and 2000 screens (which are the same). It also has TV out, though the 2000 does as well.
I wouldn't even hesitate. I'm playing Little Big Planet and LocoRoco Midnight Carnival myself right now and, really, they look like absolutely dogshit on the 1000 and 2000 screens, but absolutely lovely on the 3000 (and I assume the Go as well). Emulators also look killer on this screen.
Using a modded 2000. Best handheld ever -- can't find a reason to upgrade (especially because the 3000 isn't as hackable as the 2000....right?)
It's not as hackable, but you can use ChickHEN combined with some Gen hacks to get it running ALL homebrew and pirated games without any problems. You can't permanently hack it, as in, turning the system off reverts the system to legit mode, however, that isn't bad at all (just keep it in sleep mode).
That's still a slight downside, however, as the 3000 hacks are usually released a tad later. I had to wait an extra month to get full support back for the newest games (though they now work perfectly).