Update: By now, September 2, about a month after the initial post, there have been well over 1000 AN-2s and Y-5s identified. About 5 have been found in flight. I had no idea what I was starting, and no idea how much help I would have in finding this unique design. Thanks especially to KASSPER and Delta102 for providing the vast majority of the "discoveries" There are still many out there in high res areas, I'm sure. These planes can easily fly from unmarked dirt or grass strips not shown in the GE transportation layer.

Here are a few more images of AN-2s and a Y-5:


image from www.wingsovergillespie.org


Image from www.machtres.com


Image from www.yakuk.com


Image from http://gallery.taggesell.de


Image from www.simonb6.co.uk