CRGreathouse
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D H said:1066.
From the wikipedia article on Middle English:
1000:
Syððan wæs geworden þæt he ferde þurh þa ceastre and þæt castel: godes rice prediciende and bodiende. and hi twelfe mid. And sume wif þe wæron gehælede of awyrgdum gastum: and untrumnessum: seo magdalenisce maria ofþære seofan deoflu uteodon: and iohanna chuzan wif herodes gerefan: and susanna and manega oðre þe him of hyra spedum þenedon.
1400:
And it is don, aftirward Jesus made iourne bi cites & castelis prechende & euangelisende þe rewme of god, & twelue wiþ hym & summe wymmen þat weren helid of wicke spiritis & sicnesses, marie þat is clepid maudeleyn, of whom seuene deuelis wenten out & Jone þe wif off chusi procuratour of eroude, & susanne & manye oþere þat mynystreden to hym of her facultes.
Modern:
And it came to pass afterward, that he went throughout every city and village, preaching and showing the glad tidings of the kingdom of God: and the twelve were with him, and certain women, which had been healed of evil spirits and infirmities, Mary called Magdalene, out of whom went seven devils, and Joanna the wife of Chuza Herod's steward, and Susanna, and many others, which ministered unto him of their substance.
Certainly it's harder to go from modern to 1066 than from modern to 1400, but I think that the changes from 1066 to 1460 were smaller, year-by-year, than those from 1460 to 1510. (I reserve the right to fiddle with the precise years!)