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English also has mutually unintelligible dialects that arose within the past few hundred years. That’s an entirely different question than the question of whether a native speaker of a “standard” dialect can understand older “standard” dialects.

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True this. In the 1990s I visited California and I had to walk out of a sandwich shop because I could not make out a single word the kid behind the counter was saying (Brit with a BBC English accent). There's not one American accent, there are dozens of them, and some of them are very challenging for me. To be fair though, part of that could be influence and merging with other languages brought in my immigrant communities from Europe over the last few hundred years.

Yes, but they are categorized by phonetic mergers and splits. Once you understand which vowels tend to merge with each other (like the back vowels), it's not so hard

The most difficult ones are Scottish and Irish English, but they split earlier with some sound changes happening in the south of England in the 1600s that didn't happen in the north.

Standard Southern English and Standard American are mutually intelligible, modulo local slang

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