The first gen of most of the equipment I work with all seems to be designed in a picture-perfect lab where 'it worked fine'. But put it on the road, and set it up and tear it down every day and it craps out within a week.
But my favorite was the first gen of the big plasma TVs. Conventions loved 'em for sales pitches in the corporate booth and for PowerPoint slide-shows in the meetings and break-out rooms. But they were so obviously intended to be mounted once and only once - and in a wall, not on a stand. They must have broken a big pile of them because the second gen was easy to use.