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Leaks and flooding
Most boats do not sink at sea but on their berth, and not through a hole in the hull but through a fitting that somebody installed and then forgot.

Where it comes from
Look at the openings first: seacocks, hoses and their clamps, log and echo sounder, stern gland, rudder tube, cockpit drains. Only then the hull and its fittings. A hose that is not double clamped is a leak waiting for its day.
Fresh or salt
A finger in the bilge and a taste tells you in one second whether you are looking for a leak from outside or a burst fresh water tank. That saves half the search.
What helps
A softwood plug at every seacock, tied on so it stays there. For bigger holes a collision mat, or cushions and wedges from inside. And always close the relevant valve before trying anything else.
The pump
A bilge pump does not stop a leak, it buys time. So: pump on, but search for the source in parallel and prepare a distress call. An alarm on the bilge switch that also reports when nobody is aboard is one of the cheapest sensible things you can fit.
What this has to do with insurance
Leaking and sinking are insured perils, but the cause has a say: an aged, brittle hose is wear, a valve that suddenly fractures is damage. What applies to your contract is set out in your own policy wording. In practice: hoses and clamps are maintenance, and if you date them you can later show that you did it.