The folks at HunterOwners.com came through once again, providing better pictures, diagrams, instructions, and tool recommendations than I came up with anywhere else on the Internet. Turns out that everyone hates that fiberglass rudder support shelf... you can't see what you are doing, and you can barely feel it when you are squeezed in back there with one hand.
At any rate, they filled me in on exactly how the system works. The top nut is the packing nut; it is actually larger than it appears, extending up the post further than one can see, so that it has room to contain the packing material that is pressed against the shaft to seal it. You rotate it counter-clockwise, looking down, to loosen it up (if one were re-packing it, all the way up, when one would then futilely attempt to pick out the old packing with a toothpick or something and force the new flax into the gland), and clockwise to tighten it. The bottom nut is the locking nut, and rotates the opposite direction to secure the packing nut once you have it tight.
The folks in the forum recommended something called spoonbill vicegrips for the job, and from the picture they provided, those would have been about perfect. Unfortunately, when I got into town last night, I couldn't find any. I settle for a massive crescent wrench (which turned out to still be too small) and a large pair of channel lock pliers. In the event, only the channel locks were of any use, and they were damned awkward, as I had to try to use one hand to both keep them clamped tightly and to try to turn the nut. Toward the end as it got tight, that was very difficult indeed.
I first backed the locking nut off quite a way. As noted before, both were only hand-tight, so that wasn't difficult. I then tightened the packing nut down by hand as far as it would go, then went at it with the channel locks. A half hour later, I had it what seemed to be reasonably tight, and reduced the influx of water to a series of occasional drips only. I crossed my fingers and tightened up the locking nut against it, hoping that the rotation wouldn't loosen it, since I had nothing to hold it with, and for whatever reason my luck held and the two locked together tightly with no apparent backing of the packing nut. I went up and tried the helm, and the rudder still turned freely, so it isn't too tight. And hopefully, the bilge will start to dry out a bit.
I went and took a well-earned shower (it's super-grimy back in that space; I found loose nuts, washers, random bits of wood and plastic, and a tube of solder that all must have fallen in back there over the years) and now I am off to gorge myself at Dave's annual Superbowl party while I cheer the Saints on toward victory.
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