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Oh yeah, a 16 gig memory stick will be plenty. I, personally, rock a 4 gig and it's not nearly enough. I mean, I have 2 PSP games and 3 PSX games and some homebrew, but I want more. 8 gigs should do it for me. And as for PSX games, you need what's called Popstation. The most popular one is called PSX2PSP, and it allows you to convert PSP ISOs (they MUST be .iso) to PSP EBOOT.PBP files. With the converted file, just drop it in its own folder in PSP\GAME on your memstick. Example: If you have an ISO of Legend of Dragoon, you could make 4 separate EBOOT files, or you can mash them all into one. It's up to you. I got 4 separate files, one for each disc, to save space on my memstick - just use the one corresponding to the disc you're on. Anyways, what you would do is throw those into PSX2PSP, and it would spit out an EBOOT.PBP file. You just take that and throw it into a folder (make one called Legend of Dragoon) on your memstick in PSP\GAME and you're good to go.
...Of course, it's much easier to just torrent PSX-PSP versions of the PSX games you want.
...Of course, it's much easier to just torrent PSX-PSP versions of the PSX games you want.