CSS Paged Media

First of all, LaTeX is not really intended for unattended typesetting of large documents. ConTeXT may lend itself marginally better to this, but it will still not be on par with the requirements for automatically typesetting a newspaper.

By contrast, the combination of HTML and CSS performs way much better at automatically positioning and resizing content whilst not requiring much effort by the designer. After all, this is not surprising as this is exactly what we expect fluid web pages to do: adapting content to unknown screen dimensions.

This is why the commercial software Prince XML deserves mentioning here as a bridge from HTML to printed media.On the product's website there are several examples of entire magazines automatically typeset from HTML & CSS.

Recently, this technique received a generic name: CSS paged media. One can read more about it here.

Under specific circumstances the use of Prince XML is free of charge.

Myself, I am using the non-commercially licensed Prince XML in my automatic work flow from Pandoc Markdown over HTML & CSS to Letter & A4-sized PDF. Check out my website for examples and the makefile.

Even though I have a good amount of experience with TeX, I was unable to achieve such nice-looking automatically generated results with LaTeX nor with ConTeXt.

Moreover, the HTML, CSS & Prince XML combo is extremely fast. Whereas ConTeXt would typical require at least 3 seconds for a couple of pages, Prince XML does the same and better in a fraction of a second. So server-side on-demand typesetting with the commercially licensed Prince XML certainly belongs to the realm of workable possibilities.