How understandable is a dialect?

I was just reading on the culture of complaint in David Crystal’s Stories of English and then read in my Norwegian grammar a little on the dialects and the history of the standardization process in Norway. The latter was and is quite fraught with controversy. But it is instructive to compare that history with that of English where the focus is on nitpicking over spurious grammar features which supposedly make for unclear, imprecise and inelegant language.
Norway was part of the Kingdom of Denmark and Danish was the language of the country. When Norway gained independence from Denmark in the first half of the 19th century, some Norwegians wanted to gradually process the Danish standard into something closer to Norwegian (Norwegians, Danes, and Swedes can have a conversation, each in his own tongue, and understand each other. I’ve read that Swedes have trouble understanding Norwegians but once they get what words they are saying, they understand it just fine, while Norwegians understand Swedes just fine when they speak but cannot sure the Swedes attach the same meaning to the words they use). Others wanted to replace Danish with a Norwegian based on dialects and Old Norwegian (I have a 19th century grammar of Norwegian for English speakers that resolutely titles itself Norse, the author explaining he wants to emphasize the ancient lineage of the language). The ensuing battle still goes on (rages might be too strong a word these days) with the country divided between the compromise with Danish and about 10% of schools using a modified Western dialect-based standard called New Norsk.
Looking over the differences in the dialects, I note how similar they are to differences in North American dialects, e.g. the Southern monophthongization of “I” or “eye” to “a” and the Canadian “oot and aboot”, neither of which are cause for misunderstanding. Grammatically the varying past tense forms certainly are mirrored in common uses like “I could have did it if my dog hadn’t went into the street and got ran over.” The hilarious attempts of the grammar mavens to convince us that people who talk like that live in “hollers” in the hills of Appalachia reveal how blind people are to actual usage.
As I lay napping just now I heard an old tape of an NPR program on a bluegrass venue in Georgia. The vowels of the locals certainly qualify as dialectal, perhaps requiring different spellings. Yet we have no trouble understanding the people of Suwanee, Georgia.
The comparison between the history of Norwegian and that of English should clarify some of the reasons for the misunderstandings about language so common among English speakers.

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