Additionally, I am planning to replace all wiring for the antenna and masthead/steaming lights. Water somehow finds it way through the insulation of the wiring and into the forward junction box. Any recommendations on a high quality replacement cabling?
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I had the same problem with water coming down the cable to the junction box. I my case the culprit was the steaming light cable. I put a dab of caulk on the hole in the mast where the wires went though by the steaming light and it fixed the problem.
I have a separate Windex and VHF antenna. The cable is good quality Anchor RG8X.
The steaming light is typically a maximum of 20 watts (12V @ 1.66 amps). You are ok to use 18 gauge wire for that with less than the recommended 3% voltage drop for critical applications. Use the Ancor 18/2 Flat Safety cable (marine grade tinned).