Is now a good time to get a PSP? Which handheld do you personally prefer DS or PSP?

I think you are absolutely right about the DS and the PSP targeting different audiences. That's really true in a broader sense in that Nintendo and Sony target different audiences. I am a big Nintendo fan, but I'm also a very casual gamer. I don't play a lot of games with complex storylines or that require hours of play. I prefer the DS, but it sounds like the PSP is better for you. I'm getting one for my son this holiday season, and I'd suggest that you go get yours as soon as you can. During the holidays, I expect that they will become very hard to find.