A good long term fix that will work!!!
Almost every deck stepped mast has the potential for water leakage down through the wiring hole. As a matter of fact, if you look at the new Hunters, they route the wires out the side of the mast and then down into a wiring tube to eliminate this problem. Most people do not realize how much water can get into the mast in a heavy rain through all of the openings in the top of the mast. Here is a sure cure.First of all, the small stub at the mast step is not high enough, so when the base of the mast fills with water, it runs down the wires which are almost impossible to caulk. For the time being, drill 2 small 1/8" holes in the mast just above the depth of the mast step. This will help any water collecting in the base of the mast run off. Next time you step the mast, find a piece of plastic hose which will fit over the little stub at the mast step, put the wiring through the plastic hose and then really caulk the wiring in that hose leaving enought slack so you can put the end of the hose over the stub. This will allow more water to collect in the base of the mast before it could possibly run down the wiring even if you did not fully caulk the wires in the plastic hose and the small holes you drilled in the base of the mast will let the water run out. I have done this on my last 3 deck stepped masts and had no more water come below. It really works.