The transom felt solid on my 1969 20ft as well. I ran it for a season or two like the photo below then replaced, was surprised how solid it felt being so wet. I would go ahead and right near the engine as close to each engine bolt outside of the engine bracket go ahead and drill out some test holes and see what you have near the engine bracket. Try to not drill the test hole completely though pick one side get to the next skin of fiberglass and stop so you can fill them up a bit easier. If the wood still has a little structural integrity in the fibers maybe you can get away with another season but this is one of those subjective things where no one is going to be able to tell you if you will have a failure this year. You can fill the holes with Marine-Tex if things are looking ok and move on and replace in the future.
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