I've learned to remove the wheels and pins and store them in my trunk during long drives. The vibration causes them fall out. The same happens sometimes to the wing nuts holding the cross section on the dolly.
I take off the wheels when I trailer my dolly. I have had the pins shake out from road vibration. Also make sure the wing nuts that hold on the cross piece of the dolly are taped on to something. I have lost those bolds from road vibration as well.
Alan - Have you thought of putting some carpet or other material on top of the plywood? I would think the wood could get slippery after being outside for a while.
The mast end cap is not designed to be water tight. Generally you will get water in the mast from regular sailing up to deck level which is the water level in your mast step. (Any more will drain while the boat is upright.) With a small hole in the cap you can drain out the water after your...
Consider moving the cleat up or down a few inches on the mast and fill the old screw holes with epoxy. I did it and it worked fine. (By the way, use brand new screws.)
I recommend drilling a hole in the middle of the bottom cap of the mast to allow water to run out after sailing. While silicone and other things may seal the bottom for a period of time eventually it will leak and you need some way to get rid of the water.
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