Based on your pics, I'd go with the second one: Better overall shape, less draggy stuff hanging off the side, appears to have had at least some attention to aero drag in the design. You could make a simple and light aero fairing for the AC on top. After going past the relatively sharp leading edges of the first trailer, aftward flow would probably be so buggered as to exceed the drag of the second design.
Which would be easier to add Coroplast belly and wheel fairings to? Which has better surface texture from the getgo? Which weighs less?
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