The "How It Works" page, https://letsencrypt.org/howitworks/ , has me a bit worried. Anytime I see a __magic__ solution that has you running a single command to solve all your problems I immediately become suspicious at how much thought went into the actual issue. If I'm running a single web app on a single Ubuntu server using Apache then I'm set! If I'm running multiple web apps across multiple servers using a load…
I think it's about time for a free CA that is recognized by all clients, but you still need to establish a trust chain to exchange a CSR for a signed certificate. This service needs to be server agnostic. The barrier to adoption isn't configuration, and HTTPS isn't the only thing that uses certificates.