Why YSK?
The first person who typed “should of” probably heard of it in real life that was meant to be “should’ve”, they typed “should of” online and readers thought that it’s grammatically correct to say “should of” which is in fact wrong and it became widespread throughout the years on Reddit.
I hope something could start to change.
True. Just because “language is descriptive” (descriptivist will always let you know) doesn’t mean everyone can go freestyle with language, carelessly introducing ambiguity and miscommunication. They always say “as long as it gets the point across” but as a non-native but still pretty fluent, most of the time they don’t actually get the point across.