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@gbj_tester
Yes, in the sense that Cd is dimensionless, so the drag would be in the same proportions as the Cd if they all had the same frontal area.
Because the air has to move around it in a different way, which takes more energy. There is a particular issue with objects placed on static ground planes, which you'll notice if you ever walk past the Euston Tower; because the wind can't go under the object, it gets squished into the path going round it. It gets worse with taller structures because the wind can't effectively go over the object either; it is energetically preferred for the flow to accelerate round the sides of the building rather than climb over it, leading to higher wind speeds adjacent to tall buildings.