Caddy definitely offers a better developer experience, but I'm just too familiar with nginx to migrate.

This setup works well with Docker: https://github.com/nginx-proxy/nginx-proxy/

I'm using a variant of the three-container setup, and I really can't complain. It's quite a workhorse, handling everything from DNS ACME challenges to reasonably complex reverse proxying over IPv6 (both through the host network and virtualised networks), non-HTTP streams, and more.

The only painful part, in my opinion, is injecting nginx config fragments per host, installing plugins, and so on when you need to go low level. But I find myself doing that less and less these days.