Here is a neat trick. You can use Itunes, a free and fairly stable program available in both windows and OSX versions to organize and categorize your PDF collection. The program can auto-copy into a storage directory and allows you to group the files in various ways.

http://lifehacker.com/software/pdf/geek-to-live--organize-your-pdf-library-with-itunes-240447.php

Sadly, it will not work on DOC or RTF or LRF or other file types. Has anyone found a program that allows the storage and cataloging of these various files types?

Maybe someone could create a plugin to sync iTunes with the PRS-500 ? That would be pretty cool... We could also imagine "textcasts", PDF embedded in RSS that would autosync on the reader.

The libprs500 GUI is designed to store and catalogue books in all the formats supported by the sony reader. It will be a couple of months before it becomes stable though.

Kovidgoyal, where do I get the Libprs500 GUI if I want to test it?

https://libprs500.kovidgoyal.net/#Installation

Tried that and get "Server not found". Anywhere else?

Try it again. I just got it; but, you have to manually agree to the security certificate on my system using IE.

I use good file names on mine and subdirectories. No fancy programs needed.

Its hosted on my home server so it occassionally goes down. Try again.