For your friend wanting more aero with a prius pulling a trailer. Design a one wheeled trailer. or a no wheeled trailer on a hitch. Stability issues aside more wheels = more significant drag.
I used to race hpv trikes and always took a big hit on drag from the extra wheel when compared to bikes. I did win the class 3 years in a row. I was over 50 then and raced against a lot of younger riders.
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