@Tinido this is fun! Sadly the author does not seem to be on Fedi?
I wonder if @yvanspijk could read all this just as is… (Yoïn, spoilers ahead so if you want to play, read the OP article first.)
I first got slight troubles in the 1500s when there began to be occasional words I didn’t know. I guess I would just have to look them up in the dictionary as I need to do today for some English words. These that troubled me were distinct from those that would trouble a native speaker, for I’m German and know Latin, inflection gave me only a little pause, we had long s ourselves, and I knew thorn, eth, and even yogh and wynn.
1200 was when it mostly lost me. I don’t know Old High German, so even after I figured out the… well… double u, and identified wif as woman, I only could follow a larger part of the story, but not all of it any more.
1100, well. I got that they were to marry. That’s that. yfel was understood, and cƿæþ was clear from context.
1000, I could read more easily than 1100, as in, the writing gave me less tongue-tying, but I understood even less of the words. "næfre ne mihton fram Ƿulfesfleote" was clear but the verb of that sentence not. In retrospect (after having read the summary), ofslean is clear (seeing the dutch connection here), same for forlætan = verlassen. "deorcan stræta þisses grimman stedes" is dark street of this grim… well stede, I don’t know how to put that in English 😹 Stätte.