Don't know if anyone is still looking at this thread but here are a couple of suggestions:

1) You will never receive CG permits to run a beach cat event around Vancouver Island. I did the Van Isle in 2009 and will be doing it again in 2011. These are some very remote areas, with little to no place to pull on to a beach in case of gear failure or injuries.

2) The currents are far too strong to allow you to sail through Seymour Narrows, you would have to get a tow. This is the case also elsewhere on the course. The wind is not at all predictable during this time of year, meaning you could be swept very far away from where you want to go. For example, on a 65' boat we were nearly swept on the wrong side of Quadra Island on the leg to Campbell River, it can happen.

3) A 20' Rib is the minimum PER BOAT that would be required for support for this distance. You would need a support boat for each boat competing, for safety and gear issues.

I am not trying to shoot down the idea, it is quite intriguing. I am interested in distance/adventure racing in the NW, my wife and I have a Hobie Tiger. I would suggest if you are serious about such an adventure that you contact the Van Isle race organizers, and ask if you can participate in the 2011 event, with your own organization, up to the Campbell River stopover. This would give a good three leg event in which to "test the waters" so to speak, with other boats around in case of problems. If you still wanted to attempt a full rounding of Van Isle, then this would be a good starting point, but like I said, I think you are seriously underestimating CG permitting and support craft.