Negative on needing an obvious structural issue to have water intrusion. If you read the used boat buying threads you will find frequent reference to blisters, wet core, and delamination. These are all caused by water infiltrating the supposedly impetetrable gelcoat, or by water getting in through screw holes, tiny cracks (have you ever dropped a
winch handle?) or past poorly installed (not properly caulked) fittings, like
cleats, blocks,
winches, and shrouds. We had a screw hole on the INSIDE of our hull which, over the space of 20 some years of spashes, rain, condensation, sweat, bilgewater, you name it, caused delamination of the balsa core of our boat in a roughly 3' diameter area. Tapping the entire hull with a small (but hard) rubber hammer every few inches is the best way to find problems that have grown that big. Moisture in the hull or laminates is a precursor to possible problems later. Fixes can vary from rebedding fittings to stripping the entire hull. It all depends.