How far back in time can you understand English?

1200 is much harder but I can get maybe 60-75%:

Hit is muchel to seggen all þat pinunge hie on me uuroȝten, al þar sor and al þat sorȝe. Ne scal ic nefre hit forȝeten, naht uuhiles ic libbe!

There is much to say of all that paining he wrought upon me. All that soreness and sorryness. Not shall I ever forget it, not while I live!

Ac þer com me gret sped, and þat was a uuif, strong and stiþ! Heo com in among þe yuele men and me nerede fram heore honden.

Here is where I lose the thread.

A wiff ... wife? witch? waif? woman? ... who is strong and perhaps stiff or some similar word, comes to him with great speed. She comes in among the evil men/man and saves him with her hand. Although I could be way off

Heo sloȝ þe heþene men þat me pyneden, sloȝ hem and fælde hem to þe grunde. Þer was blod and bale inouȝ And hie feollen leien stille, for hie ne miȝten namore stonden. Ac þe Maister, þe uuraþþe Maister, he flaȝ awei in þe deorcnesse and was iseon namore.

Here I can gather a lot more but I'm guessing a lot:

She slayed the heathen man who pained me, slayed him and felled him to the ground. There was a lot of blood and bile and he fell and lay still. For he had no more might to stand. And the maister, the wrathful maister, he fled into the darkness and I saw him no more.

Ic seide hire, “Ic þanke þe, leoue uuif, for þu hauest me ineredd from dæðe and from alle mine ifoan!”

I said to to her "I thank you, lovely waif/wife/witch, for you have saved me from death and from all my (?)"

And then from 1100 I can gather that the waif/witch/woman replies to his thanks and introduces herself as Aelfgifu, which I incidentally know is an old English female name meaning Elf Gift

Any further help?

Firstly, you're conflating German and Germanic, while ignoring that the common ancestor here dates to before the High German consonant shift between the 3rd and 5th centuries, that further split the German* languages, that had already long since split from the other Germanic languages.

Secondly, my point was merely that there is a closer relationship between the Germanic languages historically spoken around the North Sea, than with modern standard German that has carried with it the consonant shift, and so if you take into account Low German/Plattdeutsch, the similarities are more visible and obvious.

I see no reason to try to mush them together, but it would be interesting to see German take the approach of Norway: Norwegian have had a few fairly successful reforms actually moving it further away from Danish in some respect, but which also in some respects have mean allowing older forms closer to Norse in the majority form of Bokmål, that were retained/included in Nynorsk.

If German did the same thing and started encouraging and allowing those of the forms of minority Low German dialects that are closer to the older Germanic forms (e.g. Dag instead of Tag, for dag/day), it might over time restore some of the continuum.

In English class at school in Norway, I went through a phase after reading LOTR in Eglish for the first time, where I'd frustrate my teacher by using words that were archaic enough that my teacher had to look them up.

> Old English thinking it would be more like German, but really it is much more like English than people think IMO.

Compare it to Old Norse, and Old Dutch, though, and there are many similarities that stand out. My Norwegian lessons very brief foray into Old Norse definitely made it easier for me to dechipher parts of Old English and Old Dutch (the latter also helped a lot by my halting German). I think a lot of the similarities comes down to learning to recognise a few of the key sound and ortography shifts, at which point they start to look a lot more similar than it looks at first glance.

The way to remember thorn: "Ye Oldee Shoppe". The "Ye" there is "þe" (the), written with "Y" standing in for þ - historically for typographic reasons, and in modern times just repeating that change.

> "ſ" is also easy to guess and I'd seen it before.

It's in use as a long s[1] in other languages too when using Fraktur style fonts in particular. One of Norways largest papers [2] still insists on using it in their header, which led someone I went to school with to insist the name was "Aftenpoften" instead of "Aftenposten" ("Evening Post").

[1] https://en.wikipedia.org/wiki/Long_s

[2] https://www.aftenposten.no/