I set out this week with new resolve and found a few resources that I'm going to try. The Coursera class through Rice U. will take the next 7-9 weeks and I'll supplement with Code Academy & Python Monk.
When I'm finished with that, I'll try to apply my glorious new Python skills to GIS. Some other free resources:
ESRI - Using Python in ArcGIS 10.1
Penn State online course
We'll see how this goes... wish me luck!