You should read Power of Babel if you like this topic!

https://www.amazon.com/Power-Babel-Natural-History-Language/...

Most of English's "problems" come from a sort of natural drift that all languages experience all the time. There's no way to freeze a language in its "most useful" form, because a billion different speakers are simultaneously pulling it in different directions. It either ends up as a sort of democratic consensus, or eventually fractures into mutually unintelligible dialects.

1. Shakespearean pronunciation: http://www.youtube.com/watch?v=gPlpphT7n9s

2. Problems that would be caused by simplifying spelling: https://en.wikipedia.org/wiki/English-language_spelling_refo...

3. Power of Babel: http://www.amazon.com/The-Power-Babel-Natural-Language/dp/00...

4. Toastmasters speech about "Manglish": http://www.youtube.com/watch?v=GDanVi6byKo (Toastmasters has its own version of English, full of over the top gestures. Also recommended, search for Singlish on Youtube.)

If you're into this sort of stuff, John McWhorter describes this theory and many others in his introductory book to (mostly historical) linguistics, The Power of Babel [http://www.amazon.com/Power-Babel-Natural-History-Language/d...].