Language history

How far back can you understand written texts in your language with relative ease?

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I can kind of understand Old Castillian.

When was Hochdeutsch invented again

16th century

Earlier than that is where it starts to get difficult.

I can read the oldest text written in French in the 7-8th century.

up to 5 century before the language is totally the same. And basically from there each increasingly different and harder to understand.
But to be honest it doesn't matter so much because there aren't so many text written in French before the Renaissance, most were in classical latin.

dunno 16th century I guess

there were hardly any texts in Polish before that

t. republican propagandist

What are the Matters of Rome, Britanny, and France, also, what are the countless romans, poems, and chronicles written in Old French.

depends on whether it was Ottoman Turkish or actual Turkish. Ottoman Turkish is equally hard to understand no matter the time, actual (common) Turkish can be understood as far back as 12th/13th century with ease, and earlier works can be understood with some lexical help.

By 'lexical help' do you mean transliterating Orkhon runes? If that's the case, shouldn't transliterating the Ottoman Perso-Arabic script provide just as much ease?