I agree that it should be a summer time trip. I did some chart work on it and you could do it easy in a month and a half with lots of time to site see and only fly about 2-3 hours a day. (150 miles per day average) Probably have a few days of bad weather and some maintenance along the way. But I really think it would be a very interesting trip seeing it all from a couple thousand feet. Looks to be plenty of airports along the route. Saw only a couple places where you need to go off course to find an airport. And with Uber and Lyft getting to a local hotel and back should be easy.
I think it's at least worth studying some more.
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