@TheBigYogurt finally managed to build a prototype of the image scoring service i mentioned when you were in NY, if you'd like to take a look: http://web.imgstamp.com:8080/#!/ It only works with landscape images and a few categories yet, but it's functional.
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Thanks, this pre-mortem is a good idea!
There's another trick I learned recently that is a bit like this. Before starting any big project, try to predict what someone you respect would say in response. Even if they would agree with your plan, just the practice of doing this will give you a very useful skepticism.
