I’m optimistic about how Mozilla, the EFF, and others are approaching HTTPS. I agree that HTTPS is hard to use now, and forcing people to use the current systems would be a barrier to entry for many people. However, they appear to be trying to break down the assumptions that HTTPS has to be difficult, and make it easy so that anyone can use it.
As others have mentioned, the “Let’s Encrypt” registrar they’re sponsoring is a great step toward making HTTPS more accessible to set up. In your follow-up, you discuss a few situations that “Let’s Encrypt” may not handle well right now, but along with the registrar, they’re also building open protocols and software that could be building blocks to address those issues as well.
But, the biggest aspect of this is to shift the perspective from “HTTPS is hard, so let’s not use it” to “HTTPS is hard, so let’s build tools to make it easy”. Projects like “Let’s Encrypt” are a good start, and if we continue with that mindset, the push towards universal HTTPS becomes about breaking down barriers, not building them up.