Claymore-I don't think that English is going to work out quite that well. Its very facility in absorbing new words is driving it to unwieldiness. If it survives at all, it will be due to a continuous shedding and regrowth, as it has been doing for its entire history. Chaucerian English is no more akin to modern English than is French to Spanish. While I will admit that the language and culture are quite adaptable, I see little difference between total adaptation and complete revolution. We change too much to last: even if it's still called America, it won't be at all the same thing as is now, which is in turn completely different than it was 150 years ago (though scarily similar to the Gilded Age).