I believe David is right about the top shot being a reversed negative, and I say that because what looks like the old Cinema is at the top right of the parking lot.
Really like the clarity of the second shot over the train station. The decline in passenger train travel is evident in comparison with some of the older Marchant photos David has published. No extra passenger cars or locomotives parked there waiting for their next run. The Purity Cafe building -- although I think the cafe itself was closed by then -- is still there as are the Terminal Hotel and Mr. Reese's bicycle shop.
No.5 looks like the Coca-Cola plant to me as well.
In shot No.8 -- the one with First Methodist in the center of the photo and the Rice Street bridge and hospital in the bottom right corner -- you can see the underside of the airplane's wing across the top of the frame with the starboard flap beginning in the center and extending to the right. That would indicate that Barbour, if he was in one of the planes from Rockingham-Hamlet, could have been in the forest service's Piper Cub or perhaps in Wingate Williamson's Cessna 182 flying west along the railroad tracks. My guess would be that the plane is a Cessna, which has metal wings with crimps in the metal flaps that are visible in this shot, rather than a Piper Cub, which had fabric-covered wings.
Good views of the high school and gym in the last two shots. Haven't seen them in a long time.
HHS Class of 1969