Regarding the Steeplechase story. I recall entering the New England 100 back when it was a "real-man's" race. New London to Jamestown, out to New Bedford the next day.
The SIs clearly stated that you were on your own, no chase boats would be provided. There was a laundry list of safety gear requirements, and all boats were inspected before the start. There was also a provision that you might be required to demonstrate your ability to right the boat if the RC/OA wanted to see that.
Not sure how much more you could do...
Mike