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I'm working on a CFEngine Tutorial to help people get started. I was inspired by Michael Hartl's "Learn Enough Tutorial Writing To Be Dangerous" talk at LA Ruby Conf to finally turn my CFEngine course materials into a book. It'll be my first commercial product so I'm excited!

Edit: added link to mhartl's tutorial: http://www.learnenough.com/tutorial-writing

As a former user of puppet and chef, I would say cfengine has a higher entrance brier. It pays the efforts thought.

Is SSH really a dependency you have to worry about though? Basically every server out there runs SSH.

SSH's major problem here is performance. When you need to orchestrate dozens of servers with many separate tasks, then the slowdown is very noticeable.