I think it's often easier because most of the nerdy complexities are via a GUI... though the web.config offers a lot more in more recent versions. And adding in Application Request Routing (reverse-proxy) and the like can get complicated quickly, it's not nearly as bad as either nginx or apache tend to be. I do like what nginx can do combined with lua though, it's pretty damned cool.

All in all, I do like Caddy's defaults and out of the box for newer tech. I haven't really tried it much, mostly out of complacency with nginx/iis in Linux/windows. And I will definitely never run Apache on a new box again.