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I agree with pidgeon that Calibre will put books on your reader in just about any folder system you could imagine. The Calibre forum is very active; they can point you in the right direction if you need help for something more complex.
If you're looking for a new reader, I think the the Sony PRS x50 series are just about ideal. The firmware that comes with it is solid, intuitive, and displays libraries very well. Adding PRS+ provides an additional layer of functionality. The screen is Pearl, which is the most advanced available right now. It's touch screen, but very matte, so fingerprints simply don't show up. Maybe you'd see something if you touch the screen while eating Cheetos, but not in normal usage.
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