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Looks to me like an idea very easy to put in practise :

- Buy some recent high-res data, maybe from DMCII (http://catalogue.dmcii.com/). You can get relatively recent (month old) data for very cheap. Only issue is to find high-res enough data. - Link the image to a gg map / OSM equivalent for geocoding - Create mechanical turk or taskrabbit to search for pools / houses without pools

Do that for one neighborhood and see if you can make a sell. No automation needed, or at least no complex CV involved.



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