With the billions that have been spent on education why can't a huge number of graduates from the last two decades manage to use contractions properly?
What is so difficult about recognizing that an apostrophe (') takes the place of a letter, word and/or space? Moreover, what is so difficult about teaching and remembering it?
A recent billboard advertised
Beach Living At It's Finest
which means that at least three people (a copywriter, an editor/boss/publisher and an advertising sales rep) but probably more let this error pass undetected or unchanged. Renting a billboard can't be cheap. The folks doing the advertising may never know that their little typo is costing them potential customers - the kind with disposable income who justifiably avoid doing business with those who can't manage to use a single little apostrophe correctly.
The you're/your battle seems to be hopeless especially among the U21s.
Your just jealous, I hear them saying. Perhaps I am, but not of their usage.