Well-written, Scott. I find myself agreeing with many of your points already, and learning a few things as well. One assertion I would add that I did not see was that PDFs are rarely a good choice for e-documentation. I cringe when I download documentation to my phone saved as PDF instead of epub or HTML, since the document's static text-to-page ration is going to require my zooming and scrolling constantly. So much easier to read a document formatted to be viewed on a variety of screen sizes!
Although it's possible I may have an earlier one stashed somewhere, the oldest one I know of is my Slackware '96 disc set from Walnut Creek. For those of you who don't remember it (and those of you who do, for that matter), the disc art looked like this: https://blogs.ua.es/labseps/files/2014/12/slack96.jpg