I ended it up a 1:1 workshop at KC Peaches yesterday evening and we worked our way through Learning Python the Hard Way.
A few things cropped up that would be useful for those working on a Window's machine
Command line
GIS / Dataset
Windows packaging
Other
If anyone has anything else to add, please comment below.
I will be running Intro to Python Part 3 workshop again, it will be on Saturday, 22nd Feb @ GameSpace Incubator, IFSC, D1. Details and tickets: http://codinggrace.com/post/75168432595/introduction-to-python-part-3
