can a wing be designed to ship in several pieces meeting that 2-part mast spec?
Yes.
Ben Hall's A Class wing split into two parts, lower and upper.
So, maybe an F-18 style with wing, self-tack jib and spin? Could it be designed to convert a standard F-18 platform with a wing sail to promote interchangability (olympic / fleet)
Easy. Just build an F18 as light as possible and then add 100 lb ballast to race in the F18 class.