I bought a fat DS at launch on Thanksgiving 2004, then traded it into EB Games for a GBA SP straight up and got a PSP at launch. Had it for 2 years before I traded it to someone in 2007, just rebought the PSP last year and got a BUNCH of games off Goozex/TRU clearance/B2G1F at Gamestop. Sold my DS and all my games to Gamestop a couple of months ago to help pay for Halo Reach, CoD, and probably Dragon Age 2.
Getting VC 2 day 1 next week and the new GoW day 1 only for all the stuff you get for a preorder.
The PSP issues are as follows: bad load times out of the gate (still an issue on some games but the digital version helps see Mana Khemia for an extreme example,) glut of direct PS2 ports instead of reworking ip's to work on PSP (see Twisted Metal, GoW, Syphon Filter, etc.), bad marketing which continues to this day, games costing too much ($40 MSRP at launch still for most), and the discovery of mass piracy options have led to the abandonment of the platform by western devs. The only games we can look forward to on the platform are Japan centric titles (Square Enix, Sega, Atlus, etc.) and those coming from Sony directly.
And the blame is not just Sony, it's the pirates also. Take the award winner from my podcast for PSP GotY last year in Rock Band Unplugged. Sold so poorly they stopped doing songs for it on the PSN and now Rock Band 3 is on the DS, which has a MUCH more limited way of adding songs via DLC than the PSP, but will probably sell better on DS.