I have a reliable 36” kayak bag and absolutely love it. Holds multiple 40” halibut (just zip it up to the tail) or a rockfish/lingcod limit no problem. Would obviously be a problem with larger seabass or sharks. It holds 20lbs of ice for a few days. Only thing I don’t like is the zipper is not leak proof so if loading into a car or trunk it’s gotta be laid down zipper side up.

After reviewing the website and watching some of the videos, I think this trip is possible. For small boats and kayakers it is more about finishing than winning the race. They do a first day shake-out from Pt. Townsend to Victoria, so that is a good test. There are two other check points along the way. They require/issue tracking devices, etc.. Looks like people that are in small boats and kayaks typically wait out the worst weather camping on shore.

Most of it is the inside passage where fast currents and wind waves would probably be more of a factor than ocean swell.
The narrows seems harrowing - I'm not sure how you could time it to avoid the strong tidal currents at kayak speed. Even going with a strong current seems like it could be bad.
I would try to peg lots of potential beach landings/campsites ahead of time, making sure there is room above high tide. 
Seems like an extra drive would make sense if possible. 15 - 20 days seems like a lot to expect out of one without issues.

You need to bring a bear canister for sure for food storage. I could probably lend you mine. One will not typically hold 18 days worth of food, unless you eat only oatmeal/freeze dried, so maybe 2?
If you see a grizzly, I would get on the yak to the water (but don't run). If it's a black bear (they can be brown) you can probably scare away, but even those might be aggressive up there.
As for fishing - it looks like all Canadian waters . You might have more time to shore fish if you are having to wait out the weather.

As far as TI AKAs go, a friend and I had one of the ties snap outside the Golden Gate and with the Ama swinging away, I made him grab it and it was like a Buster Keaton or Charlie Chaplin scene with him stretched between the boat and the Ama with his belly touching the water. Funny but harrowing.

On the into to sailing course we noticed at least 4 dead pelicans floating in the water, and the trainer was mentioning they have been seeing a lot of them recently 

Tips wise the fish should still be up on any flooded bushes/trees so flipping something weedless in there should get bit. That’s up in the arms. For the main body dragging a green pumpkin colored jig along points or deep cranking a Shad crankbait is a good bet.

I talked with my cousin in Port Townsend about it yesterday and first thing he talked about was bears. He knows people who do the race Lot of places along the way where you haul out are wild and full of nasty bears

Reminded me of a place in cal I crude-camped with a friend we had blankets fishing poles and a rifle which I was hugging all night long

Every morning we woke up with bear prints all around us some right next to our heads

Canadian bears are a different story