You should always have some form of connection break inside the mast at the base. Otherwise, with direct runs you would need to cut the wires to take down the mast, which would probably lead to having too short of wire length when you go to reconnet the wires. There are water-proof plug/sockets available, but a waterproof junction box with screwed down connections on a barrier strip would probably be the best solution.
Those clams aren't tall enough to prevent the collection of moisture inside the mast from overflowing them through the gaps between the wires they are meant to contain if the weep holes ever get plugged up with debris.
You didn't mention what year your H34 was, but from '84 on they used a different mast and the tube feeding the wires through the deck became a source of water penetration and ultimate cross-beam/compression post failures as it wasn't tall enough. Make sure yours is.
PS: Speaker-like wires = power to spreader lights?
PPS: Re-read Allan's advice and would say that it is a good alternative to connections made inside the mast itself.
Well, my mast is down now and I'm replacing everything. If I had to pull it down again, cutting wires would be the least of my concerns. I would put a terminal box inside the cabin somewhere, but I can't find an easy spot to put it. It was suggested that I put it under the seat where the holding tank is housed, but that would mean that I would have to run wires down the compression post and likely back up again and over to the port side, unless I can get wires from that seat area and under the floorboards.
I have an '86 with a Kenyon mast. I'm replacing the compression post right now due to the poor design, which allows water below the deck just as you described. I still have to track where exactly the wires that ran inside the compression post go. I'm not at the boat at the moment, but I believe one is red, one is green, and there's a few black ones (I could have this confused). They run right under the holding tank and, from there, I'm not sure exactly where they go. The speakers wires aren't for spreader lights - I think they were used for either the deck or steaming light...not sure why. They certainly don't appear to be marine grade.
Do you happen to have any links to the waterproof plugs that you recommend? I'm thinking I need to run a three-strand wire up to the masthead, my VHF coax, and my new cabling for the new wind transducer, and then a second three-strand up to my steaming light. All four runs will have to somehow make their way through my deck step. This is the wire I was looking at for the masthead and steaming light runs. I'm thinking 12-gauge should be fine?
