Very difficult to diagnose why the apostrophes do not render as intended
Good post, Brian, but I think the main point could be emphasised a little more. The tone should be conversational, informal, and friendly, as you said. (Hope the comma Nazis don't get me for that sentence).
What I do is read what I'm writing. Yes, this is something we all do, right, but how many people actually read it to themselves? Try reading it out loud (if no one's in earshot), pausing at the commas, using the words you have written.
Apostrophe misuse makes me cringe, but even worse is incorrect versions of your and you're; and there, they're, and their.
I agree with your point on parallelism, but not your example. That's because the verb ‘bought' could easily be used for the second item as well as the first – in which case it's fine to leave it out of the paragraph list
When I received the article in a gmail message, the subject matter looked promising until I read the first line of the article which offered a catastrophic butchered display of the apostrophe which read “It's time”
What a shame that the spirit of the article itself felt hollow to me when the rest of the text suffered from similar periodic spasms of unintended corrupted character display.