Here's how it works: if you have a document in one format and just want to read it on a device that uses a different format, Calibre is the tool. However (and there is one exception to this however), if you want to produce a commercial quality e-book with working TOC and other format-specific features, Calibre is not the best tool.
Back to the however's exception -- if you have a good Word doc and want most formats from it, Smashwords is your perfect answer. Smashwords uses Calibre but not straight out of the box, which is the basis for its exception. The "meatgrinder" system they've developed adds a great many custom scripts to achieve results that exceed any other method. But don't expect to buy that in a software package any time soon. That's their edge -- their proprietary scripting, an edge they deserve to have and keep. It's a large part of what makes Smashwords so valuable compared to countless other content posting sites.
So back to where I began -- if you have an e-book you'd like to read and the format isn't to your liking, there are plenty of software tools, and it appears Calibre is the most versatile, making it the most useful. On the other hand, if you are hoping to produce a commercial-quality e-book, EPUB for example, that is best done in a good text editor by a talented programmer who at least knows HTML, more is better. Either learn to program or hire someone who already knows how. Which is how most everything works in this world, you know? Like your car, learn mechanics or hire a mechanic. Specialization does have value. Anyway, in the hands of a talented programmer, then you can have a TOC and yes, even pictures with some compromises, for which you do not have to limit yourself to PDF. Don't get me wrong, I'm a long-time proponent of PDF in graphic systems, it being the perfect page container as I predicted over a decade ago. But when it comes to e-books, there are FAR better choices like EPUB.
About starting with Word, that is fine. I make lots of HTML from Word then massage the code. The thing is, make it a clean Word doc. It should use few styles, body text, chapter heading, chapter para 1, passage para 1, passage break, an italic character style perhaps (and maybe bold also if non-fiction). A few more if really needed, but if you have 72 variations of body text with override upon override applied to one style... well, yeah, the resulting HTML is a freakin' nightmare, no doubt. Fix problems upstream and the river flows clean...
William Campbell, author and publisher, DEAD FOREVER and others.
Last edited by William Campbell; 04-24-2010 at 08:30 AM.