I have been an applied aerodynamics researcher at NASA Ames for 31 years. In addition, I grew up racing sailboats,
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So I am well-acquainted with the performance of sailboats at downwind headings not directly downwind, and it is true that for sailboats, there is a significant benefit to boat speed to do that, primarily from the aerodynamic characteristics of sails. However, that effect is not in play to any appreciable degree on the DWFTTW cart, and if anything, acts to diminish the thrust on the propeller.