Selfhosted
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For me it was usually that the config that I need to serve a site with TLS is quite short, there are sensible defaults and many things (e.g. websockets) just work without further declaration. That's especially important if you want to host a container that has some lacking documentation about usage of reverse proxies, as most things "just work fine" for me.
And using a simple include directive, you can even replicate 'sites-available' and 'sites-enabled' behaviour. My standard Caddyfile just sets up the log file format and location and basic Let Encrypt values. Then it includes
/foo/bar/sites-available/*. Every deployment/container now has its own Caddyfile that just gets linked there.