Traefik can read labels applied to Docker containers (easily done with docker-compose) and setup the proxy for you as containers come and go. Even maintains the Lets Encrypt certificates seamlessly.
I also think Caddy 1 was just simpler to use in general, so it didn't matter as much. But I don't have much experience with that version, so could be wrong.
I was trying to configure the auto-HTTPS functionality to use DNS challenges, because my setup forbids any of the others, and this apparently requires plugins that are only supported by community efforts, so that's probably why I had such an issue.
The docs around configuring this were not immediately clear to me. Its like one part is over in this corner, the other over there. And the part about DNS provider plugins is off in a completely different direction. I definitely think things could be better organized. Also your one tutorial for getting HTTPS support only mentions the very basic cases. I think it'd be beneficial to see some more advanced tutorials using for instance some of the other LE challenge methods, something like this definitely would've saved me some time.
I wish there were an easier way to bind docker ports to Caddy automatically (without using dokku et al.), but for now I maintain a Caddyfile. Which, thinking of it, doesn't even require setting up a janky script for the rare times when I need to host a new service & modify the config.
I guess there's no reason to make things harder for myself 6 months in the future.
Related: https://xkcd.com/1205/