For drag calculations, I'm trying to determine the cross sectional area of an assembly that would be exposed to the free stream velocity. As the object can rotate, the cross sectional area would change. I don't need the numbers for every orientation (would be nice), but if I was able to select some specific orientations and determine values, that would be the goal. Is SolidWorks capable of giving various cross sectional areas in this manner?

For rough drag calculations I made three bounding sketches in three planes and made flat surface from them. Next you can mesure area of this plane surfaces.

For more accurate calculations I get data about orientation of each member of my structure (coordinates of three points: origin, point on longitudinal axis and point on transverse axis, third axis you get by cros product of x and y). These three normalized vectors give you Rotation tensor of member CS, after this you can find drag and lift forces on each member.