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For a book like the Python book, what features of LaTeX were used? I usually associate it with its ability to do fancy typesetting. But the Python book looks like it could be done in mostly Markdown.

lots of formatting features, easy to version control, able to convert to print book and pdf easily, fully text based thus more predictable, and so on. LaTeX can be used for any document from CV to an entire book.

Most of this is true, but I found that it completely falls flat on its face once you want to do any reasonable HTML output. htlatex is an abomination that should be destroyed in the fiery pits of hell after some long quest with a ring and some hobbits.

Presumably because LaTeX is designed for typesetting for fixed page sizes while HTML is designed for creating content that reflows to different window sizes and devices?

Not really - it is more that the various wrappers from tex to html are written in the spirit of the ancient web, rather than a transform to (another) simple, structured markup language. Somewhat odd considering docbook sgml should be a good match for modern html+CSS. I've considered writing something better, but have come to the conclusion that treating tex as output is just more reasonable (ie write in something like rst/markdown etc).

I don't use raw LaTeX anymore. Check out the new README and latest repo as I've switched to rST and full on Dexy to do the build.

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