[MrScruff]

Seems like some of the initial changes are reflecting more than just the evolving language. He’s comparing someone using informal slang “not gonna lie” against someone writing extremely formally “Hunger, that great leveller, makes philosophers of us all, and renders even the meanest dish agreeable.” which I’m not sure makes sense.

[jcul]

This struck me too, the fact that this task is so impossible.

Language changes in the time axis but also in the location and social axes. The best we can probably hope for is one snapshot in time. However this is meant to be a blogger, journalist, writer etc., through time this may have been the expected style for writing of this sort.

Especially in medieval times, I understand it may have been impossible to understand people a few towns away as the dialect could change so dramatically.

Disclaimer, I'm no expert, but I find linguistics fascinating.

Still, I really enjoyed this and I commend the effort!

[CRConrad]

I think you can make it make sense if you think of it as "writing in a speech popular at the time". Nowadays we (sometimes, often?) write the slang we speak; in the 1800s, people wrote (and perhaps spoke?) in more flowery sentences. Romance novels might seem written in stilted language to us now, but in their day they were kind of like writing in slang is now.