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Chick -

The water intrusion issues for your boat are due to lack of maintenance and care by prior owner(s). Thru hulls are the weak link for EVERY boat.

I would also pull the fuel tank cover and inspect the cavity. While it is is gel coated, if the prior owner did not take care of maintenance, it could have water on the top of the tank.

Some models of post-classic whalers have a drain from the fuel tank cavity aft. If there is a drain in the aft wall of your boat, it could be blocked.