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So it looks like PSone Classics are really getting added in again which is great!
Absolutely! I love playing PSOne classics, PSP games too. It's great to see companies like MonkeyPaw Games bring over PS1 games as 'imports'. As far as I know they still plan to bring some PSP games to NA PSN as well.
However, a big problem for me (without a PS3) is that the Vita is not able to download many PS1 and PSP games directly from the PSN store. The Crash and Spyro games are VERY surprising to be missing, and I'd really like to see Konami's games show up as being compatible. That's a disappointing issue that I hope SCEA is actively trying to fix, get on that Sony!
As mentioned, Playstation Now is likely going to be a way to play all these 'classic' games in the future, which is cool, but I'd much prefer to have games downloaded to memory card so I can play anwhere at anytime.
If VitaTV gets a worldwide release that might be another reason for Sony and other publishers to make a push to release more classics.