Hi,
you shouldn't really have to change any of your code just the
settings.py file to reflect your new system layout.
I am not sure about IIS and python, i am sure there will be a lot of
hits when you google "python iis".
Mysql should not be a problem either.
Windows is less restrictive on directories so it should be easy to get
the "uploading" to work.
I develop on Windows, but host on linux. (using svn you keep the live
system up to date).
The main issue will be running your project via IIS (never done it so
dont know).
oliver