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Let me make sure I understand exactly what you want.  Am I correct that:

a) you start with an aerial photo like #1, below; 

b) put black shapes over either each house in the image, or each plot of land as shown in #2, below;

c) and then change the background to something undoubtedly a lot more complicated than the simple white background I show.

If so, I don't see why you need to introduce the extra step of starting the shape-making process with a larger shape representing each city block or group of houses.

T