You Should Know
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Typing "should of" is a sign of failing to understand the basics of English grammar.
Eh, it's just shifting of how written work is relfective our spoken word. It's pretty rare for me to use a stronger "ah" sound when saying "would have" most of the time defaulting to a softer schwa sound, which sounds almost exactly how how "of" sounds. English has been changing and evolving for centuries. There's even major epochs like the great vowel shift. Hell if Shakespeare were around today and making the drastic changes to the english language like he did back then he'd be crucified by internet prescriptivists for using English improperly.
If you'd like something a bit more modern, Mark Twain broke english rules all the time in his writings and he's considered one of, if not, the greatest American writers.
Shakespeare did not "make" changes, he's just a very good record of changes that had taken place.