I have been self-hosting for a while now with Traefik. It works, but I’d like to give Nginx Proxy Manager a try, it seems easier to manage stuff not in docker.
Edit: btw I’m going to try this out on my RPI, not my hetzner vps, so no risk of breaking anything
You can easily get automatic renewal for nginx using certbot.
Yes, but it is a different cron job that needs to run, and you need to monitor it for failures. Caddy does everything out of the box, including retries.