I did try out iPSP a few days ago. It has a great interface for converting and copying any media to the PSP. It seems to directly tap into the user’s various iLife libraries. Unfortunately, I ran headlong into the main drawback to the PSP as a multimedia device… memory! The PSP has less memory than the iPod (with video) by orders of magnitude!
So, in contrast to the PSP (with 32 MB of memory out of the box), iPod has 60 GBs, and iTunes, however misnamed at this point, provides a decent interface for getting audio, images, and video onto the iPod. Unufortunately, iPod has very little to offer in the way of games, and the video iPod in particular has very poor peripheral support thus far… no iTalk even. In fact, because of the iTalk and iTrip, I am continuing to use a 30 GB iPod Photo as my primary iPod despite having access to a newer model.
And so the one device dream remains elusive.
Also, at this point, with the exception of gaming, iPod is the clear winner over the PSP for educational applications.