When I was working at Loyalist Township last summer I was doing some editing when I noticed something that made me exclaim in amazement: "these were taken at the same time!"
When my supervisor asked why I was surprised I told him that our aerial imagery matched perfectly with Google Streetview for a cemetery in Wilton. This isn't unusual, as one would expect, cemeteries don't change too much, but this was more than just tombstones. He came over to my desk and I pointed out that all the cars in the imagery were in the same place as in Streetview, as was the recycling yard waste across the street and a rather large pile of flowers on the ground.
What really gave it away were the cars. They wouldn't be parked in those locations regularly on the side of the road. Both the airphoto crew and Google car had both captured a burial, and since those don't typically last a long time, they probably took their images within about 30 minutes of each other. A cool coincidence that I had never thought had the chance of occurring or even detecting.
My supervisor and I immediately told the rest of our department and the other GIS analyst in Engineering. We even did some more digging and hypothesized the exact date based on when the imagery was flown and the recycling day for that street, in combination with the fact that the yard waste had not been picked up yet. We even spent some time looking for the Google car in the imagery, but to no avail.
Realising that these images were taken at the same time is probably one of the most interesting and shocking things to have happened to me in my short career. It isn't groundbreaking and probably isn't even uncommon. But it is really really neat. Cool even. And I hope to be telling this story for a long time.