I think the complexity of automation is more a symptom of the problem space than the tools. It's just a hairy problem. Computer Science seems to largely focus on the single system. Managing "n" systems requires additional scaffolding for mutual authentication and doing file copies between different systems. It also requires the use of directory services (DNS, LDAP, etc…)
I like the analogy of comparing the guitar player to a symphony orchestra. When you play the guitar alone, it's easy to improvise, because you don't need to communicate your intent to the players around you. When a symphony does a performance, there is a lot of coordination that needs to be done. Improvisation is much more difficult. That is where Domen is right on target, we can do better. Our symphony needs a better conductor.