It was exposed in a conference at "pas sage en seine 2015"[1] that almost every french banks websites use broken security because their ATMs are still running windows XP and go through the same web server.
We as an organisation like to take our time. We wouldn't welcome a new joiner with a PC on his desk. Much more fun to see him struggling for weeks with our internal IT approval processes. We happily pay millions to Microsoft to get the privilege of using Windows Xp / 32 bit systems a little bit longer (I have now almost more RAM in my mobile phone than my workstation). In fact I suspect many of the critical infrastructures of the organisation are running on COBOL. We'd probably still use CRT screens if our IT department could source them. We are certainly still using blackberries (I hope they will stash enough devices before RIM goes bust).
I just set up a site a few days ago with caddy - http://caddyserver.com. Getting certs for multiple domains was a matter of adding a single line for tls to the config, it generates a key locally, requests the cert, and installs it transparently on the first request. Pretty smooth. I hope they will autorenew without intervention, haven't tested that bit yet, but so far it was painless.
I imagine most mainstream servers will incorporate this sort of smooth tls flow at some point now that services like letsencrypt are available to base it on. I'm considering moving web server for other sites (usually use nginx) for this single feature.