I just finished incorporating letsencrypt into my hosting setup. A mostly painless process that probably took me less time then renewing my old certificate.
As mentioned in my docker quicktips article I use a mix of docker containers to serve my web content. To move to letsencrypt i simply needed to add another container in the mix. Letsencrypt-companion takes care of acquiring all needed certificates that are proxied via nginx-proxy. A few edits to my systemd services that take care of the docker container management later everything looks fine and is running smoothly (so far!).
Overall a good experience and it feels good to cross the ‘RENEW SSL CERTS’ entry in my calendar off.