It's silly stuff like "Bill said he's free Wednesday or Thursday: which slot works for you?"

Yes.

Stop being so accommodating. Some clients are not worth the trouble.

There are a lot more pluses than minuses.

The pluses aren’t interesting enough for me tell stories about on HN, so you’re getting a skewed image.

Maybe assume he's reading it as "Wednesday? Thursday?" "Yes". Meaning, he's saying yes to the latter of the two.

Ha, I would typically assume the former. Usually people lead with the strongest/most desirable option. The remainder are all technically available.

Speaking from experience with the functionally illiterate: they read this as "Wednesday....work for you?"

This is absolutely my experience as well. I used to encounter this regularly in a professional context and ended up just replying with a confirmation that "option A" was what he'd agreed to. I was never mistaken.

And it's OUR fault these people are allowed to continue existing unimpeded in society.

Just so we're all on the same page.