Django and Rails - what should I expect in a Windows environment?
I am using Django on Windows Vista and it works very well. I am using sqlite, mysql and postgres. 
mysql install is a bit tricky: I recommend to download the right binaries from the web.
I am using popular django apps and python modules without any problem. However, I've made a quick test with GeoDjango and noticed that it doesn't work out-of-the-box, mainly because of Postgis.
It's juste a little feedback. I hope it helps
I work in an environment that is totally .NET.
However, over the past few months I've been learning Ruby and Rails on the side and enjoying it very much.  I have been using Windows 7 to develop - along with Aptana - and so far things have gone better than I expected.  I have run into a few issues with gems on windows - various gems with event-machine dependencies often blow up on me while installing.  Also, deploying to Heroku can sometimes be an issue because of x86 references being put into Gemfile.lock.
The biggest issue though, is that there have been a couple of projects at work that could have been tackled quite well with Rails - except for the fact that all of our apps must run in-house on IIS.
I've recently been thinking of similar frameworks and languages such as Python and Django, and wondering (mainly just to satisfy curiosity):  
Would I have less - or more - issues developing with Python + Django on a Windows platform?  (Especially running on Windows servers)
It would be great to get some input from those who have tried both, but if you could point out some benefits vs pitfalls to one or the other, that would be much appreciated.