Re: If only it were that easy
@ Dave559 You seem to assume that only businesses use the internet. Lots of private people, hobbyists and even kids run servers and use the internet freely for enjoyment and general communications. Perhaps you're not a server guy (obviously) and perhaps you only use the net for corporate or business purposes, but please don't ignore the general public's right to basic internet freedoms.
"If the company which hosts your website doesn't already offer automated https certs via LetsEncrypt, get a new (and better) hosting company."
You're not talking about servers, you're talking about shared hosting. Not everybody buys that kind of package which is mostly (though not totally) aimed at beginners. Some of us prefer to run servers and enjoy the freedom of using the internet without paying somebody else to do the administration and telling us how to host a site. Perhaps the best way to explain it is to liken it to cooking at home. Some people like to just get the ingredients and cook for themselves whereas shared hosting is like eating at a restaurant.
Regarding moving to another hosting provider, people with dozens of sites aren't going to find moving all that easy. That said, hosting providers have a problem here too. No doubt they'll be able to do some fancy scripting to provide LetsEncrypt to each of their customers in some transparent way, but it's going to take a while for them to get it done.