Bad advice
That is a new one. The keel has bolts imbedded that are bolted on in the bilge area. 5200 which is one of the best sealants is used to seal the keel to the hull. It takes alot to pry that sealant apart. I am the king of caulk and when I applied this to a fiberglass arch on a larger boat one time, I cussed myself into the water when I fell off and when getting out still cussing, a seagull pooped on my head. Now lets look at the boat on the trailer. The bow eye is hooked of course and you have a strap around the back of the boat so it will not bounce on the trailer. With the above, I seriously doubt that. Now one other testament to the H 23 wing. In 1987, I was bringing one back on a two lane hwy.. The tractor trailer passing came left of center and struck the boat. The boat came off the trailer and went sailing down the road on its keel at 55 mph and then did a twist hitting an embankment. The keel never came off and there were no cracks at the keel to hull joints.Does that pretty well sum it up.If the boat is in the water and you observe water coming up through the keel bolts on any boat, then it is time to drop a keel and reseal it.Crazy Dave Condon