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Are the masts solid grown, or glued up from sawn timbers? It's possible that they are effectively trees that have dried out in the boat. In that case, the shakes, assuming that there has been no serious water ingress, are not an issue. By now the masts are properly seasoned, and it would be possible to fill the shakes with epoxy, microfibres and microballoons before sanding them down and covering them with one layer of fibreglass, after which they would be coated with some more epoxy and then painted. I would follow David's suggestion of enlarging one or two of the shakes to see if there has been any damage, first.
The fibreglass flag poles sound interesting, but a lot of flagpoles seem to work on the principle of 'what bends don't break'. However, the mast on a junk rig needs to be very stiff, so it would be worth seeing if you can find any photos of these flagpoles in action, flying a big flag on a windy day. But USA is also, apparently a good source of alloy light poles which may be stiffer. Look on the fora and Junk Information/useful links for more information on these. There is also a mast database, from which you might glean some useful information.
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