Mostly classic boats here from the 60's-70"s so I dont know if you will get the replies you are looking for...most of the older hulls had drains placed in the stringers near the transom for just the reason you are here. Water will get everywhere and anywhere in a boat due to what ever so there needs to be drainage to the bilge and out the transom for that reason...not sure about your live well leaky gasket or something else..
strick
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"I always wanted to piss in the Rhine" (General George Patton upon entering Germany)
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