It's very frustrating to work with Windows. The lack of a POSIX compliant shell in the standard distribution is what's holding it back the most.

Mac OS 9 and prior was also super frustrating to work with for similar reasons.

Both Chef and Puppet have made big strides with Windows support recently and people are using them in anger. Might be worth reading the following:

http://www.opscode.com/blog/2011/05/24/chef-hearts-windows/ http://projects.puppetlabs.com/projects/1/wiki/Puppet_Window...

Times are changing. For the better if you ask me ; )