Earlier quoted context omitted.
Yes.. 50% chance of getting it right every time, even though it feels like less than that! It doesn't help that some motherboards put the USB ports upside-down for some inexplicable reason, and when it's dark you can't see the little USB logo on the cable anyway.
Oh, it's not so bad once you take advertising sub-clause of the spec into account. That's the hidden clause that states the USB logo will be on the top of a properly-oriented plug unless you're Microsoft or Logitech, in which case your corporate name is allowed top-billing, so to speak. Of course, if the slots are oriented vertically...
Also doesn't help when the lighting's not so good and you have a USB logo embossed in black plastic on a black plug with the manufacturer's logo embossed in the same way on the other side. Trial-and-error probably isn't as bad as squinting at it trying to figure out which side is "up"...