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I read this book about a decade ago for college! I remember finding it fascinating.

On complexity, the important factor is probably contact between different languages--specifically, adult second language learners. Adults have an impaired ability to master languages, so large numbers of adult second language learners tend to lead to simplification of languages. English, for example, seems to have lost its case system when it had a large influx of non-native English speakers settle in the British Isles (iirc my class on the history of English). These (mostly) men took English wives and had English children who copied some of their fathers' idiosyncrasies in their own speech, including likely their fathers' non-mastery of case, eventually eroding the case system to basically nothing.

You can see somewhat similar process still happening with some of the only remaining case markers, "who" and "whom". Even native English speakers can't reliably remember which one they're supposed to use when, and so each following generation is even shakier on how to use them and so stop making any distinction.

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