Hey everyone, sorry I didn't mean to leave this thread hanging but a lot's happened since I started this project including a career change which has kept me busy. Have meant to finish this for a while.
Long story short, the channel seems to have fixed my CB jamming problem. After putting everything back where it belonged, I was able to consistently raise and lower the CB over a dozen times with no issues whatsoever. Here in this photo you can see the CB back in the trunk w/ the downhaul line sitting comfortably in it's groove. A huge improvement from before.
I haven't taken her out on the water yet. That will be the real test but I'm optimistic that I've solved the problem.
As a sidenote, it's fascinating to see the CB mechanism in action with the boat out of the water. Couple of observations:
1. My CB won't fully retract unless I give the uphaul a swift tug and keep tension on the uphaul. The extra momentum helps get the board fully up. Otherwise there's too much "stretch" in the system to fully raise the CB. I've gone to marking the uphaul with a piece of tape so I know when the CB is fully up.
2. Likewise at full extension the CB sits well past vertical. This can be seen in the below photo where it looks to be at least 20 degrees forward of vertical.