Well I used to be a .NET guy after I switched to node.js Windows Server 2008 was my daily bread. Over the past few years I learned how to program linux servers in all flavors, just so that I could run node.js.
Since Microsoft has been heavily supportive of node.js within their Azure hosting, as well as Visual Studio, I have been poking around little bit and the development setup and user experience is actually not all that bad :) You can now very easily install node.js on Windows Server 2008 and even get some basic project setup from Visual Studio 2010 Express.
Power Shell actually behaves very close to shell, well not quite, but for using basic node.js it's good enough. You can use the package manager, the "ls" command still works, if you type node -v it does give you the latest version. There was nothing like this when I started doing node.js, which forced me to become a linux guy, but now, maybe I would get just lazy and use Windows Server 2008 as my node.js hosting/dev platform :)
The nice part is that you can actually run node.js through IIS, which will take care of your domain routing, probably some error handeling too. Here is a tutorial that shows how to set up your node.js website on IIS.