Thanks for the response, that's really nice to hear!
I'll probably check out the more recent versions of Caddy as well, admittedly they're most likely a rather painless experience for most folks when compared with Apache/Nginx, though I've also heard good things about Traefik, which is even integrated in K3s as an ingress.
I guess most web servers are workable for a variety of use cases with a bit of effort, though I definitely reminded myself why people weren't exactly the biggest fans of the Apache config syntax just recently.
It's much smarter now.
Caddy also doesn't stop if a certificate can't be obtained. When did you last try? Maybe a big was fixed but it would have been YEARS ago.