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Linksys NSLU2 Network Storage Drive, with modded firmware it pretty much becomes a whole linux computer where I'll make it host usbhostfs. It has 2 USB ports where in one I'll plug in the drive (with a ZIF->USB converter ripped out of a 1.8" hdd enclosure) and the other will plug into the PSP's usb port. Amazingly, a whole guide for how to do this already exists at http://irshell.org/forum/showthread.php?tid=1087&page=1 which is what I plan to follow. The motherboard to this probably won't be able to fit in the PSP without major mods but the only smaller embedded linux systems with USB host ports I can find are over $100.
Are you sure the Linksys thing even fits inside the PSP? How about the powerdraw?The Linksys thing got mentioned before but I think it failed at the size of the thing, It's rather big.
You might want to check out a 2-way OTG enclosure and a 2.5" hd to 1.8"hd adapter. I read an article of it working, maybe you'd be able to fit everything in the case... http://www.akihabaranews.com/en/news-10939-The+PSP+compatible+2.5%22+OTG+HDD+case+is+here%21.html
This is the way. But expensive...