Some manufacturers indeed mounted the port upside down (not typically on laptops, but on other devices). When the port is vertical or even in a horizontal surface, people can have trouble working out which side is meant to be up. Some manufacturers (Logitech was one) made their cables with an embossed logo of their own on the side opposite the USB logo, sometimes even without the USB logo. Pretty much nobody knew about the logo thing.
Even without all that, the feeling of being slightly misaligned with the port and the feeling of trying to plug it in upside down are hard to distinguish, with many port mountings, so people assume they've got it wrong and switch orientation.
Even without all that, the feeling of being slightly misaligned with the port and the feeling of trying to plug it in upside down are hard to distinguish, with many port mountings, so people assume they've got it wrong and switch orientation.