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Honestly only losing 10% and being at 37mpg with a loaded trailer is extremely good already. I would personally refrain from adding height to the front just to allow slope (unless you need that wedge of space) because you are trying to minimize both cd and area, adding area just to slope may not be a net benefit. I think the gap is too great to assume close coupling. I assume your extra tools travel beside or on top of the scaffold, accessed from the back. I would consider making your box a squared shape, as low as reasonable to fit your supplies. Then you could put an add on to the front that adds radius to the trailers leading edge. And maybe a trailer tail type add on to the rear door, which could flip up to open out if your way. You could do an add on to add radius to the front of the fenders, and run the back of the fenders sloping in to the rear of the trailer. But given how good your mpg with the existing trailer are, I wouldn't fret about it too much.
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