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I do however have the advantage of studying old and Middle English reading Bēowulf (old English) and Chaucers Tales of Caunterbury (Middle English) in their original text. Got to admit it took a while for some of it to come back to me after all these years but I got there in the end (mostly)

Thank you for reminding me what happened in the 1300 to make English English: Chaucer. Odd that Dante is so much more popular as the two men created their respective languages but English did so much more than Italian over time.

Not a native speaker, but also stopped at 1400. I'd guess that if you know German, you can probably get further. It would be very interesting to have a spoken version of this.