The British B.E-2
Anyone piloting this plane knew that it wasn't going to last. Its engine was a disaster and the gunner seat was in front of the pilot, so navigation was difficult. They were easy targets during World War I.
The Starship
This little jet was supposed to be absolutely mind-blowing. In reality, it was forgetful. The turboprop engines and carbon-composite design made it look and feel great... at first. As the flight went on, pilots would start to notice that it was sluggish and uncontrollable.