Tom,
I'm not sure I can say I've been shocked by the way a routing looked, but I have been shocked to see sometimes how different features like bunkers, fairway widths, and green orientations look in two-dimensional from above.
Over this past winter Joe Bausch and Kyle Harris turned me on to an online site that has aerial surveys of PA from the late 30s and early 70s called
http://www.pennpilot.psu.edu/ that is just a tremendous resource and has been extremely valuable to some of our research....much like the Dallin Aerial collection at the Hagley Museum in DE.
I have to tell you that the first couple of weeks after they showed me that site was probably the closest I ever came to having Jen leave me and work fire me at the same time!
It takes some getting used to, but it's fascinating and addicting. it's really great for looking at NLE's like Trydeffrin, Roxborough, the old Huntingdon Valley, the old Olde York Road, the old Cedarbrook, Chester Valley pre-George Fazio, and a slew of others.