Strategies to keep Agent configuration in sync (Provisioning, Windows)

During the last years I made good experiences with provisioning TeamCity Agents on Linux. Puppet does a great job with this and my experiments with Chef were very promising, too. In my current project I am faced with a Windows environment and all my beloved provisioning tools doesn't work as smooth as I was used to be using Linux.

How do you keep your Agent configurations in sync under Windows?
What are your strategies managing your Agents?

During my work as build manager I often have to login into every single machine via remote desktop and do the wanted configuration changes. For example:

• Java JDK Update
• Installation of external tools (e.g. Database-Clients, PsTools)
• Visual Studio installation
• Changing Maven settings.xml
• Changing VM Options for Agents
• Windows Network configuration

What about using the VMWare Plugin with vSphere? Does this work with Windows? I think about Windows licensing issues when launching multiple instances of the same image.