I’ve been looking into using IronPython within PowerShell, here are some resources to get your feet wet.
I highly recommend you watch this PyCon presentation by Noah Gift.
Here is another PyCon presentation on IronPython by Dino Viehlad.
I already posted this one but here is a presentation by Jim Hugunin.
There is also a book worth checking out, IronPython in Action by Michael Foord and Chirstain Muirhead.
Iron Python’s documentation page has some good resources getting you started using IronPython, including documentation for integration with .Net and Silverlight frameworks.