The issue of the cutout leaking is sufficiently addressed in Winnipesaukee's post. Pretty unlikely. However, new boats are shipped with the drive units separate and they require assembly at the dealership. Part of that assembly is the bellows. If that should come apart or tear, you have a big leak that can overwhelm the best bilge pump. I would put money there.
Another remote possibility is a cooling system connection failure which could pump lots of water into the bilge in a short period of time.
Still, I am betting on the bellows.
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