Regarding #1, NGINX has created a project to make ACME integration easier. It is quite new, so I doubt it will replace your use of Caddy, but it is worth consid

Regarding #1, NGINX has created a project to make ACME integration easier. It is quite new, so I doubt it will replace your use of Caddy, but it is worth consideration. https://github.com/nginx/njs-acme https://github.com/nginx/njs-acme