Given that he's apparently relaying something that actually happened, Bernstein can't be strawmanning it. In fact he can't be strawmanning it at all, as Microsoft Word doesn't make arguments or claims. You appear to mean something more like "Bernstein is incorrectly portraying how Microsoft Word works." But as I said Bernstein presents this story as something that actually happened, not a hypothetical example, so I guess what you actually mean is "I suspect Bernstein is making up this story"?

Regardless, Bernstein does in fact address this criticism in the note added yesterday. Yes, it has automatic list numbering, but in order to achieve the desired formatting, the users had, instead of altering the formatting appropriately, removed this automatic numbering, because Microsoft Word doesn't make these sorts of distinctions clear and explicit.