Where punctuation should matter is over comprehensibility.

In the boys trousers one, context might help, and so does correct,appropriate punctuation.

There is a story I can't lay my hands on about someone whose (not 'who's), whose life was saved because a Queen moved or added a comma to an instruction from the king.

These debates will ever go on because of the inevitable yin/yang tension between the need for some rules (to aid comprehensibility) on the one hand, and the stark fact that language changes (because people are creative, there are are new meanings discovered for which new forms are required).

I'm fighting a marginally successful campaign to oppose the misuse of "that begs the question of.......", where the speaker actually MEANS "that raises the ques........". It's working, by showing that it is a misuse (If I say 'Parallel lines will never meet because they are parallel',THAT'S 'begging the question'),partly by pointing out better formulations e.g.'raises the question', and partly by sarcasm,"I thought you lot were hedgemecated".
I mean working in that some of the offenders seem to have given up misusing "begs the ques....". Including some of BBC 5 Live.

You can raise the hads sequence in the following context.
The editor asks two apprentice printers to come up with alternative fonts for'had had'(which you'll have to imagine cos of my technophobia). One of the apprentices is Hadley , Had to his friends.
"Jim, where Had had had 'had had',had had 'had had'. Had's 'had had' had had the editor's approval. I've used apostrophes and full stop - er - for -er- clarity.

Amos, please forgive me for earlier signings-off as A.

Auto.