Man, I started with Apache back in the day which is just nightmarish to manage for simple projects imo, then moved to NGINX, which felt a bit better but still not super intuitive, then NPM, which did make it significantly more user friendly.
Then Caddy came along and swept me off my feet, I still can't believe it's as dead simple as it is lol. I tried Traefik for a while because it sounded super interesting and I do love the idea, but it brought a lot of the complexity back with it for admittedly very neat docker integration.
Went right back to Caddy after I moved away from docker as a whole and I couldn't be happier, I just find it so pleasant to use. Just pure KISS goodness!
So I guess my ranking goes Caddy > Traefik > the rest