I have a simple Python script that runs in a console windows.
How can I ensure that the console window is always on top and if possible resize it?
If you are creating your own window, you can use Tkinter to create an "always on top" window like so:
from Tkinter import *
root = Tk()
root.wm_attributes("-topmost", 1)
root.mainloop()
And then put whatever you want to have happen within the main loop.
If you are talking about the command prompt window, then you will have to use some Windows-specific utilities to keep that window on top. You can try this script for Autohotkey.