Running Python & Django on IIS
There's two issue here, technological and psycological.
Technologically, yes, it's definitely possible. In fact, Django has a wiki article about this. Google also shows a lot of similar tutorials. Apache and IIS can also run on the same machine (I'm actually doing that right now from a development machine).
The bigger issue will be psycological, in the form of backlash you'll get from the other developers. I agree that Django kicks the pants off ASP.NET, but you're probably going to find that an ASP.NET shop is going to be married to ASP.NET and will likely ignore your suggestion to try anything else, much less Django.
We've been running django on IIS for a couple of years using PyISAPIe. It's a fairly big site, about 150,000 users. We're moving to linux/apache though, partly cos PyISAPIe isn't great.
Case in point - WebKit browsers don't work well with it, it seems to mess up the chunking. That's tolerable for us as we are allowed to limit our users to FF/IE7+, but annoys me on a mac as I much prefer Safari to FF.