I could not stop him.

Dad insisted on bailing out the "Dream"

UPDATE: What lessons do we learn from this?

LESSON 1: Water runs downhill and water is heavy.
As previously discussed here, here, here and here, not to mention previous Titanic history. If stored outdoors, cover preparation should take this property of water into consideration.

LESSON 2: There is bad weather in the U.P.
When storing the "Dream" for the winter during the dry season in August, it is important to think very hard about Upper Peninsula weather in September, October, November, December, January, February, March, April, and May. This includes typhoon-like thunderstorms dropping enormous quantities of water in very short periods of time. Sleet. Hail. High winds. Massive amounts of very heavy, wet snow that stays around for very long times. "Massive" as in 12 foot drifts. "Long time" as in snow that falls in December may very well still be there in March - 12 feet or more under the most recent March snow. Also it gets cold in the U.P. Really cold. Which means that pools of water stored in the top of boat covers turns into shards of ice, and canvas/vinyl covers turn brittle and can be easily shredded by said heavy, sharp shards of ice. Also:

If you use a boat cover as pool liner, bungee cords will likely not take the strain of the weight.

Canvas boat covers make very poor pool liners, even before the really bad weather starts.

I have drained the pool liner/boat cover. Again. I have placed a makeshift pole under the cover in the hope of preventing it from becoming a pool liner (see lesson 1 above). Again. This is not a solution. But perhaps it will suffice until a better solution is devised when the boat is stored next August.