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I'm no aero expert, but I would guess that the trailer with the wedge shaped front end would be better due to the fact that its front end will be closer to the airflow coming off the vehicle in front. It also has more storage space.
I notice you have too steep of an angle on the rooflines of both designs.
Rather than have a pointed front to the design, you will most likely see more benefit if you flip your design backwards and have it boattail at the rear.
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