Tim, there should have been plug in connectors between the mast wiring and the wiring going through the deck and down the compression post. With these connectors in place, it is not a big problem to unplug them when the crane picks the mast up a few inches. Sometimes a yard will cut the wires just because they don't take the trouble to pull the loose wire down out of the mast and look for the connector. If you need to add them they're a common item from West Marine or elsewhere. I'm a firm advocate of keeping that wiring protected by the mast and the deck and compression post. to run it outside the mast at deck level is to ask for trouble that is just not necessary. In rewiring my H33 mast I found that someone earlier had just caulked the whole bundle of wiring and coaxial cable solid where the wires go through the deck step, evidently trying to exclude water from going down the compression post but making it very very difficult to remove the wires. Once the mess was cleaned completely out, a messenger line can be sent down through the compression post by fastening to one of the existing wires and then pulling it out at exit hole in the bilge. The messenger line can then be used to pull new wiring up the compression post and out at the deck step. To keep water from going down the wiring in the compression post, I installed an idea I read somewhere in a sailing magazine. A piece of tubing perhaps 3" long ( I used 3/4" thin wall copper with the ends filed to take off the sharp edge) is inserted in the hole in the deck step and down into the compression post. The top of the pipe extends perhaps an inch above the top of the step casting. The tubing is caulked all around its perimeter but the tube itself is left open for the wiring, effectively keeping water out of the compression post. The picture I've included shows this a little clearer perhaps.
