The issue with glass over the skeg-hull joint is not curing or flexibility in cold temperatures. It's one of access and sequence. You stick the skeg on to the hull with 5200 and bolts, then want to glass over the joint, but the rudder went in before the skeg and there is about 1/4" between the two. You can't glass over the top end of the skeg-hull joint in that space. There is no access. So you glass over effectively three of four sides of the skeg to hull joint. Water seeps in from the unglassed top end during the summer, collects behind the lower end of the glassed over joint, then freezes and expands in the winter and pops the glass off the joint and/or it finds a way between the skeg core and fiberglass and causes delamination.Dalliance's solution for reattaching the skeg sounds right on. But, for cold climates, why not the 'glass? Too cold for good curing? The 5200 will be much less flexible in cold water than the 'glass will be. Just use plenty of MEKP and keep it warm as it cures. This is what God invented Harbor Freight heat guns at $14.99 for.
How do I know this? When I bought the boat, it was evident that the P.O.'s glassed over the joint had failed -- multiple times -- and skeg was delaminated. I didn't understand why at the time and had the same repair done, twice, by local glass experts. After a few years, I gained more confidence in my own knowledge and observations of the boat, eventually put 2 & 2 together, and insisted no more glass on that joint. Problem solved. If there is a way to glass together the top end of that joint without access to it, none of the glass experts I consulted offered it up.
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