"I'm not trying to say anything, I'm just sayin'. . ."
It's nonsense from the "Sopranos".
But, screw it! You wanna hear it, here it is. 500 miles is not much of a distance for a sailboat. Dozens, probably hundreds, of monohulls make journeys of many times that distance annually. There is a veritable migration of boats down the eastern seaboard each spring.
I'm not sure what the distance standard over time is but 180 miles in 24 hours rings a bell.
So one interpretation of the Tybee would be that the difficulty is an indicator of the unsuitability of the boats being used.
I'm not saying it isn't difficult or that it doesn't take a lot of skill. I am saying you're using the wrong boat. Hence the design questions.