Would Shakespeare have failed English 101?

The class I detested throughout high school was English. In university I took a critical thinking course for the sole reason that it was the only alternative to an English class.

For some silly reason though, a lot of people expect me not to hate English. Amongst my former high school classmates, people seem to guess English as my major about as frequently as they do my actual one. I read more than most. I tend to like Shakespeare. I subscribe to a word-of-the-day email list. I also seem to blather on in written form more than a lot of others.

Why hate English, you ask? There are a number of reasons...

• arbitrary grading: The grading on any writing assignments I was required to submit throughout high school was consistently inconsistent - it seems that some like the way that I write and some don't. Some years I was consistently at the top of the class, and others I was probably close to the median. I could take a good guess as to what my final grade would be simply based on the teacher assigned.
• silly assignments: I believe that fiction is meant to be read, not to be analyzed to death. 'nuf said.
• inane rules: English is one area where I think rules are meant to be broken, and this is why I would expect Shakespeare to have failed English 101. He's credited with quite a large number of contributions to the English language, and one does not make contributions by sticking to a rulebook.

  One of the books that I'm currently reading is On Writing Well.

  This confirms what lexicographers have always known: that the laws of usage are relative, bending with the taste of the lawmaker. ... In the end it comes down to what is "correct" usage. We have no king to establish the King's English; we only have the President's English, which we don't want. Webster long a defender of the faith, muddied the waters in 1961 with its permissive Third Edition, which argued that almost anything goes as long as somebody uses it. (p. 40)

  Rules in English are seldom absolute as many claim. Consider an episode of the Grammar Girl podcast:

  [There] are some confusing situations when it comes to apostrophes. For example, [A bunch of people] asked how to make a singular word that ends in s possessive. I know that this is a raging debate even at the highest levels of government because [two listeners] sent me a funny article describing U.S. Supreme Court squabbles over making the word Kansas possessive. Words such as Kansas that end with an s can be stumpers when it comes to apostrophes.

  Is it Kansas's statute with an apostrophe s or Kansas' statute with just an apostrophe at the end? Justice Clarence Thomas wrote the majority opinion and prefers to leave off the extra s, referring to Kansas' statute with just an apostrophe at the end, whereas Justice David Souter wrote the dissenting opinion and prefers the double s of Kansas's statute with an apostrophe before the final s.

  So who's right? ... Unfortunately, I have to admit that this isn't a hard-and-fast rule; it's a style issue.