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One of the biggest stumbling blocks that new users run into is how calibre stores books. Calibre is not just a program that catalogs books and converts them; instead it is a book manager. Everything you could do with your old folder/filename tree system can now be done from within calibre plus a whole lot more. To do this, calibre uses its own simplified folder/filename structure to store e-books, added covers, and other meta data used to sort/find books. Instead of the traditional (and highly inefficient) folder/filename tree, calibre uses tags, also called metadata, to identify sorting criteria.
When you import abook into calibre, it makes a copy of that book, then allows you to add tags, such multiple authors (I have one book that has 15), genres and multiple genres, search words, series and subseries, publication date, ISBN number, date added to calibre, etc. You can even create custom categories for custom columns. If your old folder/filename structure is consistent, you can even tell calibre to do much of that automatically. It can also go online to look up some of the information. It will also convert books to other formats and can load them onto your reading device for you. It can also be used to create printable lists of your books. With calibre, one can search for a book using a variety of criteria and/or sort books by far more variables possible than with a folder/filename structure.
The part that really trips up new users is they still want to access their books from a folder on the computer and are dismayed because calibre uses a simplified structure to store them that makes it hard for them to find what they are looking for. With calibre, one no longer needs to access their books from the folder they are in and trying to do so runs the risk of messing up calibre. Worldwalker, one of the contributors here, likens the calibre library folder to a black box that is to remain umtouched. Everything you could do within the folder can be done within calibre, only more efficiently and with more flexibility.
If a user is uncomfortable with allowing calibre to totally take over your book collection, the user can always just keep their original folder/filename tree in its original folder and treat it as a backup. I confess to doing that although I trust calibre enough that, if I start running low on disk space, that original folder is history. If a user decides s/he doesn't want to use calibre anymore, calibre can be used to recreate a folder/filename structure that will probably be more consistant than your original one.
Calibre does have a bit of a learning curve but there many wonderful users (and the developer himself) on this forum who are willing to step up and help new users. I know they have saved my ample asset many a time. If allowed to work in its own way, calibre will do more for you in more ways than you will ever be able to do with your old folder/filename tree.
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