In 1944, Keesler Field, Gulfport, Mississippi, my father was in command of the air-sea rescue craft, and wangled for me a visit to a B17, but only on the ground.
He had a trip in one from Keesler to St. Pete, Florida, and the pilot spent most of the trip at 100 feet, chasing cows; my Dad never flew again after that in anything!
In l956, flew on a DC3 in Mexico, the trip was from Chihuahua to Casas Grandes. The pilot was a full blooded Tarahumara Indian; the door to the cockpit left wide open....and the descent to the airstrip tucked between a couple of substantial mountain ranges was memorable....
An Eastern Airlines Electra, engine coughing and spluttering on the taxi to takeoff at Washington National. Captain came on blower and announced to the pax "I suppose you have noticed that we're having a little problem, so we have changed our mind about leaving for Boston" and they rolled out another Electra that worked well enough. And another Electra, flying across the mountains in Puerto Rico, passing through the middle of a nasty cu-nimb, the passengers all praying sincerely....
But on this thread I am most impressed by all the exotic gliders mentioned. Nobody yet mentioned the Schweizer 2-33, which is a real dog.
I prefer to fly aircraft that other people have flown extensively and thoroughly,
say the J3 on floats, or the Supercub. Now there is a well tested design!