I forget, is it 36"+ where the gap really starts to hurt aero?
It's a tough situation, making it as close as possible without risking hitting the trailer when backing up, going over bumps and dips, etc. Perhaps the best solution is some sort of flexy fairing that can close or at least partially close the gap without damaging anything... I seen some attempts at that on tractor/trailers but not at the consumer level.
I'd call Sven's proposal (c)- it looks quite good... now put radii on the leading and upper edges.
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