Tim, how does Iron Python 'integrate' with .net, after a quick look I couldn't find anything definite to say whether it runs in the clr or through the python interpreter still.
The reason I ask is that if it's still interpreted I don't think you will have much luck working as closely as you like, either you will have to create a command in .net to call a method in your python scripts or get a python script to call a .net command - swings and roundabouts really...
I know it's not the solution you're after but perhaps you can create a 'pyrun' command in .net say that asks the user for a method to run from python and runs it. To make it more like a real command the user can create a 2/3 line lisp that achieves the same as a real command, just create a lisp for each method. In fact you could get python to write such a lisp file quite easily as you know
.
Anyway, food for thought, hope you work it out.