Possible
Hello there,
It is easy to get one halyard in without trouble, relatively easy to get two, and things get exponentially worse after that. If it is possible to remove the masthead you have the best chance, as you can thread a messenger in (we push them in with a length of standing rigging wire), then secure the messenger under tension, so it stays out of the way. Then you rotate the mast so the next messenger can lie on the bottom, and repeat. With the masthead off you can shine a bright flashlight in, to make sure you aren't snagging lines. Run the messengers right out the ends of the mast, and then fish them out of their halyard exits.
If you can't get the masthead off, or if things are otherwise problematic, try to get at least a couple in, so you can go aloft after the mast is stepped, and use fishing weights or the like to lower messengers in from aloft.
Fair leads,
Brion Toss
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