I dont believe it is. I believe its a 3rd class lever making the fulcrum the keel, the top is the force (man at the top), and the jack stand is the load. That keel is not coming off the ground, and its not likely to skid until the hull contacts the ground, if at all. I believe the jack would simply push away allowing the boat to fall over.
Of interest is that even using your lower calculations, the man can easily produce lateral loads at the top of the mast that exceed the loads generated by a 100 mph wind.
In any case I just cant see how on earth its worth the risk. My life is worth more than any boat, and certainly more than whatever is on top of it. That jack slips and the boats going over, and the man at the top, 60 feet up, is going to have a very short period of time to contemplate his death.
Im not interested in the math, but I wonder what kind of velocity the man would reach at the top of the mast as the boat went over. Or, if the mans on a rope at the mast head, and the boat rolls over and slams into the next boat, will he twirl around the mast a bunch times like a tether ball before the mast breaks loose?