Afternoon Eric, I have a feeling this is one of those # 4,999 of 5,000 on the plane. I've never seen one exactly like the rubber stamp before, but I haven't done much searching.
I wonder if it was inconjunction with another event like a State Fair. I would imagine that the majority of covers flown were philatelic in nature. This would be a different type of flight cover, since it says "flying post office" I think there were postal employees sorting mail bags much like a RPO or HPO.
The American Airmail Catalogue, 5th Edition. Lists this as US Governmental Flight #266. Different colored cachets were used in different cities along the route with some repitition. Value is listed as $1.00 but this edition of the catalogue is over 30 years old.
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