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Yep. A bit of the DT material with the front cut off, and then opened up to 31.7mm (I'm assuming you're going for a 1" fork) would do nicely I would've thought.
I agree with tester about the TT though - I can't see stiffness being and issue, and given that vertical stiffness is guaranteed from the tube shapes, I would've thought a flat oval TT, with the thick plane being horizontal, would be best.
P.S. Also agree with tester about the external headset cups - the thinner HT is a worthwhile trade-off.
Trailing edge, surely? A teardrop shape is as aerodynamically efficient as it gets, with a rounded front end and a pointy tail. If you look at any fast road or TT bike which has had wind tunnel time, it'll have a rounded front edge on the HT and then a tapering section behind it.
The majority of the drag doesn't come from the air hitting the rounded front of the head tube - it comes from the vortices from the trailing side of a round tube which are eliminated (or at least substantially reduced) by a tapered trailing edge.