Yes, It matters quite a bit. If you notice the evolution of vehicles, it isn't just the angle of the windshield, it is also about the radius from the windscreen to the roof. This radius has gotten much larger on modern vehicles. The air is going to be moving and have a certain amount of "Momentum" when it hits your "Whale Tail", the way it is moving will have a fairly large effect on how it performs. If the air has been ramped up quickly, it will have a harder time coming back down to your rear enhancement.
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