Two good points, first I ran an 82ft schooner and never had an issue with the COI inspections. I have nothing but very happy clients I "coached thru their COIs.
The Coast Guard COI doesnt' address the current state of the vessel, hull moisture levels, etc, it only addresses the equipment carried, and periodically the hull condition, not the deterioration up to the failure point. That is where the "Surveyor" comes in for insurance purposes.
The "T Boat" inspection checklist is at http://www.uscg.mil/d9/sfoGrandHaven...t%20Inspection
If it doesn't come up, go to USCG T Boat Checklist.
One of the key points is to have a good Log book, or books, one deck log and the other a Training Log. The Coasties can tell right away if you were pencil whipping your training or really doing it. Life goes down hill from their if you pencil whipped it.
Yawl ought to come to World Wide Marine Training for a class! www.wegivethetest.com