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Hi Bret.
For windows there some pretty good editors, easy to use. Take your time to try them and customize them to your needs.
Also there are some IDEs but I would not recommend you :-)
The setup for a windows environment is described here also be sure to install all the windows packages requirements for askbot (virtualenv, python-pip, your database driver) some of that is documented on the oficial django documentation.
There are plenty material to learn python/django online to learn python use this book and for django there are some books but a good start is to read the official documentation online.
For cheap VPS service you can use VPS link or Lowendbox
I hope that it helps!