I don't recommend Chef unless you are a software developer who knows ruby. Chef is designed for software developers who want to manage IT infrastructure. Not for SysOps people who are the ones that actually end up managing it. It tries to treat IT infrastructure like code which is counter intuitive to how it actually works which is more like just data.
Puppet is more friendly for SysOps people imho but still can be complicated.
The good news is that there are other options as well. Less so for windows but projects like Puppet do support it reasonably well.
