I can relate to the TLS termination issue. It is difficult to provide a self hosted version of a web app with a sensible TLS setup.
The best is almost not to do it at all. Just have a docker image serve http/1.1 and document that a reverse proxy is required to expose the service.
There are simply too many ways to do it and every sys admin/hobbyist has their own preferred way.
For the anonymous and authenticated caching issues the author goes into, I think once again it is useless for self hosting. Just embed a performant web server like nginx for example that is pre configured to serve static files. Use proper headers, and predictable/simple paths. Self-hosted versions are going to be low traffic and just need to work.
Have advanced settings for more control, but keep the default simple and working out of the box with minimal dependencies.
I don't know what you're on about. Just run Caddy and it does it all for you.