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Shapely a nifty little Python library for geometric objects, predicates, and operations. It allows you to issue PostGIS-ish operations outside a database context for Pythoneers and Pythonistas. It's based on the widely deployed GEOS.
- Schuyler's BetaShapes Python script rock for creating neighborhood clusters.
- Mike's Skeletron for simplifying linework.
Clean your topology before asking Shapely to operate on it. You must have 100% correct topology or Shapely will complain.