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Reading left_adjoint's reply to my missive on punctuation spacing[1] reminded me that LaTeX is not exactly ideal for me. I used it to generate my undergraduate thesis as a PDF, which was great -- I generated reference arrows in the side margin that formed a sort of "choose-able path adventure" of poetry. Sadly, I lost the LaTeX source to the book, but I think I still have the PDF sitting around somewhere.
ANYWAY, I agree that LaTeX is a "crappy system to try and introduce people to." Everything from the typesetting of the *name* and its *pronunciation* (seriously, it sounds so dorky, and the pedantry surrounding the "correct" pronunciation is ridiculous; on the level of "gif" I'd say), to the -- admittedly *very* expressive -- obtuse typesetting language is hard for a beginner to even understand. These are reasons why Markdown was invented.
For a while now I've used Pandoc, which leverages the ease-of-use of Markdown to allow easier authoring of LaTeX files -- though still, much expressiveness is lost. I guess it's *not* an easy problem if you have very specific typographical needs -- it'd take as long to set it up manually as it does with LaTeX, honestly much longer.
I do agree with the CSS argument though -- one of the best things of the Web is the separation between content and presentation; it'd be really cool to be able to have like, a user stylesheet for PDFs generated by LaTeX, or to be able to drop in other styles to match the whims of the moment -- I'm thinking for resumes, but I'm thinking a lot about resumes lately.
Actually, reading through left_adjoint's post again, I *would* recommend Pandoc as a document preparation system. It's sufficiently expressive that you can hack in all sorts of extra stuff with filters and writers and templates and cetera. It's a lot of work on the back-end, but once you get something good it works pretty well. I used it and a Makefile for my personal website for a while. I should actually go back to that.