Re: 1989 23' Seacraft.
I would not necessarily worry about the transom rot. You will experience cracking(especially) in the corners if she is fllexing. You will get cracks way before it gets critical. Point is that it may not be anything to worry about. Your scupper thing is something to look into because your transome could not hold that much water to make it list. You may have some water trapped somewhere. Then again it may have always been that way. My Hydra-sport started to list to starboard. It was becaiuse the 2 batteries on that side were replaced with 2 that weighed about 20lbs more. Just enough to change it's attitude. This winter unscrew any screws in the transom and inspect again. Make suer you are using a good sealent when you put them back in.....in the spring. Let it dry out all winter and see what gives.
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regards......Nick
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