Yeah Caddy's developer experience is unrivaled when it comes to setting up SSL. You don't have to run Certbot or manage certificates manually. If you give it a hostname to proxy to, it just handles certificate management seamlessly in the background.
The real killer feature for me is the Cloudflare module. It allows you to use the acme DNS challenge, which means you can test your SSL setup without exposing your server to the public internet.
certbot has dns plugin for nearly all DNS providers including Route53 and Cloudflare. I have been using LE certs on the nginx server on my developer environment without any issues ,other can copying over the certs.
Certbot is fine, but it’s nice to have that functionality built directly into the reverse proxy as opposed to having to configure and update multiple tools. I would ideally like to see Nginx integrate a subset of Certbot’s feature set into their code base especially given that offloading SSL is one of the primary use cases of Nginx.
The real killer feature for me is the Cloudflare module. It allows you to use the acme DNS challenge, which means you can test your SSL setup without exposing your server to the public internet.