In the past I've used PCI Geomatica to do something similar using the softwares classification functionality. Are there some tools/tricks in ArcGIS that will partially automate the process. I remember reading somewhere about rasterizing an orthophoto and assigning values to rooftops, which polygons where then created from those values. I can see there being issues in trying to automate the task as there will surely be some inaccuraces do to color, obstructions, image quality, etc.
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