If you have the original scuppers, take a very hard look at the stbd one. The brass corrodes through, then the wood block around it rots, then it leaks in...
The port one on my 23 had a slow leak from that sequence and the block was jello. The stbd one had just started to rot. Both are now replaced with fiberglass pipe. If you can get to it, try sprinkling baby powder around the area - makes it easy to see slow leaks.
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