[Bagger Lance]

Although Bagger doesn't think that the waterskier analogy is useful in trying to understand the release phenomenon, I think that he is not thinking of the waterskier analogy in the correct manner. He was talking of water resistance, when one should ignore water resistance and consider the situation from the following perspective.
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Jeff,

You've put significant thought and effort into this so lets explore the boat analogy one more time. I've just invented some magic dragless skis so we that we can continue. Likewise, I can put on ice skates and you can pull me across a frozen lake on your snowmobile in order to reduce the drag effect of plowing water in your skiing example.

First a couple of questions:
When the skier reaches point C what speed is he traveling?
If faster than the boat, does he pass the boat?
If he passes the boat, how far does he go before ceasing to accelerate?
Check out these cats who are looking for the maximum acceleration point.

To save time, I'll answer the above.

The skier will travel at the same rate of speed as the boat when he reaches point C. In other words, somewhere around point B he loses the ability to accelerate and momentum will carry him to point C as he decelerates to the speed of the boat. If he had a head start like the ski jumpers, he might be able to pass the boat from momentum alone. Somewhere between point A and point B (a 22.5 degree angle), he will not be able to accelerate much further no matter how much he angles the ski. In other words, if you are going the same rate as the boat while at a 22.5 degree angle to it, you will be hard pressed to gain any speed to get to point C no matter how hard you lean into it.

In the golf swing, we are talking about wristcock faciliating angular momentum by use of the flail or left wrist. Why doesn't the clubhead overtake the hands (boat) or decelerate when nearing their inline condition in a good swing?

Because the golfer transfers all of that wristcock angular momentum into his turning left wrist which is #3 accumulator roll power. There is no skiing analogy for the transfer of wrist cock momentum into roll power.