It's not "of" it's " 've" - a contraction for have. I should have, I should've. Now if you're complaining that people are spelling it "of" then I'm right there with you

That's up there with people who don't know "cannot" is one word or that "a lot" is two.
And I think with the "heighth" thing Tremula was trying to say that they're
still saying it the way people did in the 17th century just like the Northerners who still use thee/thou/thine even though the rest of us consider it archaic.
The bookshop I worked in had a cafe and the cafe people, when off the floor, would often make fun of the "expresso" drinkers. My favorite jokes were variations on needed their espressos delivered express!