Jake,
We run our Tiger with the rig raked well back and leave it set - along with the spreader rake and diamond tension, regardless of wind conditions. Seems to do OK even in the light stuff so I don't think rake is too critical. Our crew weight is 328lb
My theory: Raking the mast forwards kills pointing upwind and makes little difference downwind with the chute. On the Hobie 18 without a chute it was a different matter - we used to rake forward in the light stuff and back in a blow.
Chris.