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
I admit I don't sail nearly as often as the rest of ya'll, but I've never been inspected or asked to demonstrate any seaworthy skills. I also was the only dork on the Steeplechase course with all the listed equipment my first run at it. Nav lights, anchor, air horn, vhf with SSB, etc. So much stuff I almost didn't have room for crew!
