Update My question is a duplicate of Extracting centerline of a Complex-Polygon in PostGIS/Python (though if anyone has a programmatic solution - that is, not ArcGIS but rather Py, C, Java, etc. - I would be interested).
Let's say I have shape such as the below:

From this shape, I want to perform a negative buffer that produces the following:

The rough idea was to perform a negative buffer that exceeded the diameter of the geometry at any given point. This does not work, though, and leads to an empty geometry.
How might I perform a geometric operation on a shape so as to impute its centermost points? Is some form of negative buffering a reasonable approach? Or, is there a more well-word path to achieving the spline of such geometries?
Any chance someone's already done the heavy lifting on implementing this in vanilla Python (aware it will be slower). Either way, this is the solution!
– kuanb Aug 14 '17 at 18:46