I'd take that over what we have now in a heartbeat.
My time isn't worthless, but for a personal web-site I am already "wasting" tons of time on it, and what is 5 minutes more? Better than a $60/year certificate.
StartSSL is too terrible. Let's Encrypt doesn't exist. And CloudFlare requires you to use their entire service for the free certificates.
But couldn't it be ad support for how little it costs? Just watch this 5 minute video then get a free domain certificate.