One more thought ... do not use your lightweight 3DLs for this race.
You grossly over estimate the budget for my racing program. My newest sail is a used J/29 Mylar main that I scored for $140!
The forecast is now up to 30-40 but diminishing alter in the race. In squamish we see those winds regularily, but never the steep waves that develop in the Strait; that is my biggest concern... I don't feel like breaking anything (see budget comment above).
I searched this site for info on what others had done for emergency steering system; there is a thread but it did not have solutions. I think a combination of dragging a drogue off of the primary winches and the Spin pole lashed to my bilge cover as a rudder will suffice. Any thoughts?
My tactician has lots of experience with this race, most of the time in his Catalina 27 and he won his division in '08. That gives me a little more comfort. Sphincter is still tight though