Newbie Questions about how it all works

There are a couple of things relevant here.

  1. Currently, Let’s Encrypt supports http-01 and tls-sni-01 verification. Both methods require access to either port 80 or 443 to the exact domain you’re trying to get a certificate for. Once you passed a challenge, I believe the authorization you get for your domain is valid for 10 months, i.e. you could get certificates for up to 13 months. As far as I know the client doesn’t yet make use of this, and requests a new challenge/authorization every time it runs.
  2. In the future (hopefully soon!), Let’s Encrypt will also support the dns-01 challenge. With this option, you don’t need to expose your service to the outside - it’s enough to change some DNS records. This is probably the easiest option for intranet sites where you need an external CA. This won’t work for domains like .local - Baseline Requirements force Let’s Encrypt to only issue certificates for ICANN domains (those found on the public suffix list).
  3. Probably even further in the future, Let’s Encrypt might implement proof of possession challenges. It has not been decided in which cases this will be necessary, it might be opt-in for domain owners, or only necessary for high-profile site. The way it works is that you need to sign something using a private key that’s been used for TLS on your domain before. But don’t worry about this yet until all the details are settled.
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