So I'm getting a PSP. It's my first from Sony, aside from walkmans and what not. I have the extra bucks and I thought it wouldn't be too bad. My girlfriend and I both have to wait a lot. We deliver about 700 papers a week on a car route. So we have to wait sometimes a few hours in line while our papers come down. That's the time we really use our DS and Gamegear. I wanted something a little more fun than Gamegear. I actually considered on buying another DS, but meh. I'd like to have something different.
Its a great hand held that can play just about anything up to the n64 on it. I recommend getting a 2gig memory stick off of amazon.com for 30 bucks. You need that if you want to put stuff on the memstick. The ones that come with the psp are only starters, not much can go on them.
Read up on downgrading the firmware and try to get the custom firmware by modders, not sony. This has a ton more features and options. Also pull out some of your fav ps1 games because you can load them onto your psp.