Here is the winners archive.
http://dish.andrewsullivan.com/vfyw-contest/
Some of photos aren't too crazy or offer a landmark that is recognizable if you'd seen it before. But most of them offer very little in terms of knowing where to start unless you've got a huge body of contextual knowledge you can draw on.
A couple ones that I had absolutely no idea where to start with:
http://dish.andrewsullivan.com/2010/08/17/the-view-from-your... http://dish.andrewsullivan.com/2014/08/19/the-view-from-your...
I imagine the CIA/NSA has a crack team of a couple dozen people doing this exact job.