I'm thankful for this discussion.
Our old HF antenna was inside the foremast; the new one will be closer to radio and tuner, in the chimney to starboard of the main mast.
My thoughts to date have been to use insulated tinned marine cable of about 20mm^2 or heavier, and I hadn't though to put it into a rope core, but it seems an elegant way, for thin cable at least. I should look up the tension it can take.
I had planned a shock cord arrangement to soften any snatching loads. I fully expect it to slap the mast loudly, and for that reason had settled in advance for taking it down, illogically, when it's rough. Better maybe to move my planned base point farther to starboard, risking its looking like a shroud.
For a conductor through the deck, I haven't drilled the hole yet, but want to embed a bronze rod in epoxy through the 3" deck and drill and tap its ends to attach a cable terminal for the antenna and the tuner. And insulate...
Hope the the ideas continue to roll in.
Cheers,
Kurt