One point about the iPod and the PSP...
While the iPod does have the "cute", "status", and "geek" aspects going for it, those weren't the only reasons the iPod has sold as well as it has. The iPod has one very practical feature which puts it far apart from most other MP3 players on the market.
The iPod can hold an entire music collection.
I think this is an aspect of the iPod which folks have been overlooking when comparing it to the PSP. The iPod succeeded by offering something no one MP3 player did, but I don't see the PSP any sort of special advantage over the competitors (DS and GBA). True, now that the iPod is popular, folks are buying it for a myriad of reasons... but would it have ever taken off if it weren't for the amazing storage capacity?