The wheel can make constant contact with a flat surface because all points are at the same distance from the center, so your center stays at the same height. But a wheel will not do as well on a non-flat surface. So for example your road surface is a series of bumps of an exact shape. The surface of each bump is the same length as a side of your square (yes, square) wheels. You will ride nice and evenly over that surface, while you’d be bumping like crazy with round wheels. This is because the surface plus the square wheels kept your center at the same height.
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