Previously I had written my CV using a word processor. I don't know the state of the Microsoft suite since I'm on Linux, but I'm yet to come across any application of this kind that does not have a bad interface, particularly when it comes to styling.
Just recently I discovered that browsers can save web pages as PDF and so the course was set!

Extending the Static Site Generator

I had to implement support for multiple input paths, since different sections of the CV will use a different set of inputs. Nothing too complex but it did lead to some major restructuring of the top level code, which handles application input parameters and all the setup for generation.

Input arguments begins with -i follow by identifier name, followed by path to directory.

-i Name /PathTo/Directory/

In addition I also added variables to identify if the current instance has an uneven or even index. I'm using this to toggle the background tint for every other entry.

<div class="Body">
<!--An input scope named "Input"-->
[Input]
{
	<div class="Section[:uneven]{ Tint}">
	<!--...-->
	</div>
}
</div>

In the above example, the Tint class name will only be added for instances with the uneven variable defined. Instances with an even index will have the variable even defined instead. Indices are determined after sorting ny date.

Closing Notes

I'm quite happy with this setup. Styling is much easier now with CSS and there's a lot more options for design. Still the most significant perk is the automated workflow.
All content is stored in plain text files independent of any document format, enabling multiple generated files to reference the exact same information.
Adding new entries is just a matter of adding another text file to the appropriate folder, filling in the required info and running a script. Most likely I will use this for personal letters as well.

And here's the end result. Thank you for reading!