I started with caddy because it seemed to have the least complex config file even though the documentation lacks examples which I found really annoying when troubleshooting or trying any less basic stuff. I also found certificate related issues really hard to fix.

Now I run nignx-proxymanager as a docker-container which unifies nearly all services into portainer for updating therefore making it easier to keep my stuff up to date. nginx-proxymanager is also much easier imo on the certificate side of things. I create wildcard certificates for a few domains and select the right one depending on the proxy I add. I also use forwards for a few of my shelly-devices which don’t seem to work with proxies and make it easier for me to access them via a domain instead of memorizing a growing number of IPs.