I did not like the idea of wire connections in the Mast base, but I wanted to be able to disconnect the wires should I need to remove the mast from the boat.
Here is my solution.
The Mast step has holes with pipes inserted. The idea is that if water gets into the mast and accumulates, the pipes will be above the water level. The base of the mast has weep holes for any water in the mast to flow out onto the deck and overboard.

Hoses are attached to the pipes. Wires run down inside the mast and form a loop at the base to allow water to drip off the wire before it can run up into the hose.
All wires come through the deck into the cabin and are terminated at a block. This area has remained dry since 2016.
A chase was designed to cover the wire cables. Radar and VHF antenna cables are run from the mast to the nav station. They are continuous and will need to be addressed separately should I have to remove the mast. This was done to minimize signal loss.