What I struggled with most in setting up things with caddy was the context for a config statement.

I could usually find the config parameters I needed, but I had no idea at what level of nesting it was and in what context it was used.

I would have found it incredibly useful to have a reference caddyfile for every parameter so I could see it used in context and then just strip that reference file down to what I need and go from there.

In the end, I just went back to nginx and dealt with Let's Encrypt myself since that was what I was most comfortable with and decided learning this new thing wasn't worth the benefit at that moment for the specific project. I'll probably revisit it later this year.