[yetanother12345]

> So it's just generating a markdown document from my Word document and dynamically renders that to HTML.

Ages ago (probably more than 15 years or so) I generated HTML, even multi-page web sites from within Word itself, using VBA. It required some proficiency in VBA but Word already had a structure that you could translate with different classes of headings, font modifications, etc. - so it wasn't exactly "rocket science" either. I did the same in Excel, but here more focused on autogenerating pseudo "db-driven" sites than on prose.

Typically these would be "intranet" apps, but I believe some may have been exposed to the www. Being static sites, security was like any other pure HTML site.

> I still don't see who would use this for their site.

My customers were in marketing. They already used these Office tools and they found it a real advantage that they could just continue to use these tools.

This was before WP got to the dominant position (and level of user-friendlyness) it has today. It's still possible though.