If you have to integrate with all that Windows stuff, you may be better off using Windows-native tools. On the other hand, that doesn't mean you have to use C#.

If you have to integrate with all that Windows stuff, you may be better off using Windows-native tools. On the other hand, that doesn't mean you have to use C#. You might want to look into IronPython or IronScheme. You can use all the .Net libraries and Windows tools that let you integrate with all your checklist items cleanly, but you can use it from a more powerful dynamic language.