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I just replaced the wiring to my steaming/deck lights (halfway up the mast). As I also replaced both lights with LED, I went down to 16 gauge wire (I think the old wire was 14... and untinned!).
My mast had 2 conduits inside: one going halfway and the other to the top. Because of this, I think it would be *very* difficult to rewire with the mast up. I had to remove the base of the mast in order to make the sharp turn from the end of the conduit to the exit hole at the side of the mast.
Edit: You might consider not replacing the masthead light at all. A battery powered LED lamp hanging somewhere on deck would serve as a fine anchor light.
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