It's crazy how much some sony decisions fucked them hard on the looong term. It's the umd thing, in first place, that not only was a bad decision for the psp (lots of technical problems and umd movies tanked bad...), but became a poison for it's successor 6 years after that.
But they could have avoided that by making the "passport" program available worldwide and making it like $1 per game. There is NO excuse other than greediness to not allow people who already bought the game to be able to play it on your successor device. At least not if you want it to remain competitive in comparison to the competition.
iphone 4s playing the same apps that people bought on their iphone 3g....3DS playing DS games...Vita is releasing in competition with this kind of environment. Is it really feasible to force your loyal PSP customers to pay another $10 per game for PSP games they already owned just for the privilege of playing those same games on your new $280 system? (system plus bare minimum memory)