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If the shaft, bushings etc are fine I wouldn't even consider removing it. Save that fun project for when you have no choice but removal to solve the problem (usually worn bushings).
Dave Finnegan
builder of Spindrift 9N #521 'Wingë'
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Agreed. Try and repair the rudder in place, unless shafting or bearing issues require its removal for other reasons.
Note that a very large majority of fiberglass rudders with construction similar to yours contain water. In my former profession, I tended to be far more surprised to discover a dry spade rudder than to discover that one contained moisture: the moisture issue is just that common. Since these rudders were built in two halves and then conjoined around the rudder post, leaks over time through this joint are common.
In most of these instances, the mere presence of water alone is not in itself structurally significant. Over time, stagnant water in any structure is never a good thing, but my point is that it doesn't mean the rudder is ready to break and fall off either.
Drill a few holes and let things drain naturally for now. Drilled holes are easy to repair, so don't be shy about it. Use these test holes to better determine the internal, structural condition of the rudder, and determine your course of repair action from there. If you need to drop it, so be it...but don't start there till you know you have to.
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It will take you through the process so you would know what you are in for. I wouldn't recommend it unless you have bushings to replace or other work that requires it.
My vote is to remove it. I got a CAL 25 this summer on the hard and the rudder was all spider webbed from years of sitting waterlogged in central NY winters. There are no bearings in the rudder tube but I'm going to squirt some epoxy and graphite in there next year to get rid of a little play. Mine came out easily.
Laval, Quebec and nearly all the rest of Canada is likely to be colder than most anywhere south of the border; Ceto should not resist taking the thing home, if it really needs work, and working in the warm. And it will dry better/faster leaning against the furnace.
Spade rudders seem to come out relatively painlessly once you've gotten the fasteners/slip joints on the post to move. Figure out what the thing is hanging on and what turns it, support it, provide enough space underneath (by digging or by lifting the boat), remove the fastenings, remove the support and Bob's your uncle. Complications include the fasteners, slip joints, corrosion or reduced clearances in the bearings, alignment. Every manufacturer is different but at least the fastenings are visible.
However, Ceto's boat has a gudgeon; it's not a spade, and there's only a cm or so vertical clearance. There're as many ways to do this as there are manufacturers however, either the top end comes apart or the bottom. Island Packets have massive, obvious gudgeons and exposed bolts. Others have gudgeons neatly faired into the keel and flush fasteners; some of these are puttied over and have to be searched for. Others, like Alden Challengers, come apart at the top with various tricky ways to remove the rudderpost from the rudder. You have not mentioned the boat make; if you're lucky there's a website for them.
I think I'd only worry about repairing the thing if there was obvious failure (what is that 'bullet hole' in the picture?). Drill tbe drain holes in the top and bottom and hope that the water trapped in the foam is reduced enough to preclude freeze-thaw damage. If you've seen the rudder swollen in winter, or cracked, or weeping goo, then maybe the repair comes up the priority.
I had major evident problems on the NE 38s spade rudder; see Photobucket; search Quetzalsailor. Major effort and I shall see what it looks like when the boat's pulled this season. I had minor evident problems in the Morgan 27's spade rudder; I removed all dad's repairs and Morgan's concealing mess, perforated the thing at 1" centers, dried it out over winter and with vacuum bagging in the warm springs' sun, glassed and faired. It appeared fine for the ensuing 9 years we owned the boat.