If my belief in his chances were worth a dollar, and he could go around the world on my belief, He won't make it 5 miles out of the bay.
His wife and his mother in law seem to be very supportive, kinda makes me wonder how much his Life Insurance Policy might be worth. Tripping along a little further down that path, kinda makes you wonder what his insurance carrier might think if they knew what he was planning and looked at his equipment.
There is a reason insurance premiums are based on "risk factors" like cholesterol levels and tobacco use.
Anyway, I believe that the Coasties might wanna have him sign a disclaimer allowing them to charge him for any rescue efforts made on his behalf, and make him post a bond to cover those costs before they even let him out of the harbor.
Fiscal realities might prove more discouraging than safety concerns.
But hey, I live in Colorado, what do I know.

Stephen