This is a display of arrogance and lack of empathy matching the Chrome team's article.
There is a sizable "old web". Built by amateurs. Think people writing web pages in Microsoft Word and FTP-ing it. They're not web developers or sysadmins and have absolutely no idea what we're talking about when we insist they should just install certbot.
Many of the owners may not be reachable anymore or in the worst case, dead.
I object to breaking the old web. I object to the assumption that behind every website there is a competent tech team, perpetually upgrading whatever others decide to break from some ivory tower. And whilst I don't need convincing of the security benefits of HTTPs, I worry about the centralizing force that it is.
Take out Letsencrypt and Cloudflare and you destroy the internet. We're practically begging for it.