Ooh wow, that'd be awesome to see - good luck man.

My suggestion would be to make it as visual-based as possible. Perhaps do it like this: (from an end-user perspective)
1) Pick a projection vector (ie, the simple version would be [+/-] direction, [x,y,z] axis, but if possible any vector would be best) and a radii from which the locations of the verticies in the insignia polygons can be projected (ie, they get projected from that vector till they hit the hull)
2) Define a level of subdivision for the projected plane. Basically this would either be 0 or 1 where 0 means you get a two-polygon plane, and 1 means you get an eight-polygon plane. Each vertex of the plane is projected separately so the idea is the plane follows the contours of the hull at the specified area.