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A significant number of my books will be scanned paper books (images only; I don't have time to run them through OCR then edit them) which average 15-25MB (Atlas Shrugged is 62MB) so there is no way I wpould be able to fit my entire library onto a reader. Fortunately, I really feel no need to. All I really need, when in town, is the book I'm currently reading plus the next one I want to read in case I finish the current one while away from the house. If going out of town, I may put a couple more books (or more if it's a really long trip) on the reader so I won't run out of reading material, even if one or two turn out to be duds. With that few books, I don't need to worry about organization.
I've searched high and low for an application to organize my library on my desk top computer and, so far, haven't found anything that comes close to what calibre can do. It is pretty geeky and has a bit of a learning curve but the user forum here on MobileRead is very helpful and, if needed, they can lead you through anything by the hand if needs be. Just don't be dismayed if they throw out advice that's over your head. If you ask, they will go into more detail for you (they must think I'm a total computer moron over there, mostly because I am).
Calibre is different from most, if not all, programs I tried in that it organizes by use of tags instead of a folder and tree structure. The advantage to that is one has far more options for searches and organization. One downside is it does create new files of your books and keeps them in its own folder (without touching the original file). This makes a lot of users nervous, especially new ones. Its not that big a deal but if one is paranoid or just attached to their old folder and file tree system of organization, just keep your original files in their original folders (like I do; yes, I'm paranoid) and just ignore calibre's. In fact, you should never mess around in calibre's files; any changes you need can be done within calibre (I keep calibre's library folders hidden so I won't accidentally mess with them; out of sight, out of mind).
In addition to cataloging your books, calibre will load books onto your reader for you, download news feeds for installation onto your reader, and convert non-DRM books to other formats if needed to be compatable with your reader. It also has a fairly nice e-book viewer for reading e-books on your computer. There are features I don't use so can't bring to mind right now.
Calibre is highly customizable. Once can add, show or hide, or delete columns at will and even add user customized columns. Each column is sortable. Searches and search parameters can be saved for viewing later. If you want one genre of books to be completely separate from your other books with or without different columns displayed or more than one user on a computer has their own libraries that you don't want mixed, you can create separate libraries. I have three: e-books, songbooks, and comics. Switching between libraries is fairly simple.
Calibre is still under development, with upgrades coming out roughly once a week. It isn't necessary to download each upgrade if the version you have works fine for you but there are new and improved features coming out all the time so it's not a bad idea to keep up with it. The developer will accept suggestions for improvements and new features and frequently implements. If you are a geek, you can even submit code for addition to calibre.
Oh, did I mention that calibre is free?
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