Python is a viable option for this task, and would make it easier to port to other OSes from Windows. However, it would probably be easier to do for Windows in AHK, or AutoIt, as they are tuned for that environment.
I would suggest a three staged approach. First, mock-up the whole thing on paper or with your favorite drawing program. Figure out the workflow. Work out what info is needed and when in the process it is needed. As well as how you wish to display it. Second stage would be to prototype it with AHK. Get a GUI built, but don't worry about making it perfect and provide basic functionality. For the third stage, get as much feedback as you can from other users and decided if you like AHK enough to continue with it or to try Python (or something else).
Just a note for you or others that may be reading and interested in possibly doing something like this in Python. If you want to interact with Windows close to natively, use Mark Hammond's
Win32 Python Extensions.