I got every major DS re-design as it came out but only jumped onto the PSP during the 3000 era. The PSP having PS2-lite level experiences absolutely melted my mind in a way that the DS did not. I loved the CFW community and all the fun ports and emulators people developed for it. The PSP came out in a pre-iPhone and pre-iPod Touch world, so having a small widescreen device that could play videos and browse the net was enormous. The only thing that's come close to capturing my interest in the same way has been the Steam Deck OLED, which is wonderful.

But in retrospect, I think the DS ultimately had the superior library and its games have "aged" a lot more gracefully. A lot of the best PSP games were scaled back PS2 experiences, and there's not much reason to revisit them when your phone or chinkheld can emulate real PS2 games instead. The PSP had its fair share of quirky, unique experiences, but the DS had a seemingly endless amount in comparison.

Not sure about "cool kids vs spergs" but here in Australia all the popular kids definitely had PSP's with GTA Vice City Stories while all the dorks were playing Pokemon on DS.