The past few days, I've been configuring a website to use HTTPS with Let's Encrypt. (on a beta invite.) I blogged my experience.
I don't think we (as a community) have understood how LE is going to affect us. I was thinking of it as delivering free certificates, but in fact their main emphasis is delivering automated certificates.
What this means is that to take full advantage of Let's Encrypt, LE client software will need to be integrated into the web platforms we use. And that won't happen unless the priority of doing so is made clear, via mechanisms such as the Library Digital Privacy Pledge.
I imagine that most libraries will NOT want to use Let's Encrypt until that integration occurs. However, once it occurs, certificate maintenance and renewal will cease to be an issue.
President, Free Ebook Foundation
Founder, Unglue.it https://unglue.it/