Here's how it works on the 28.5
I have a 87H28.5. Inside the bottom of the hull are several ribs, which have the effect of damming water from flowing from any point to the deep bilge, which is at the forward connection of the keel. The deep bilge has an electric bilge pump.The shower and the ice box on my boat drain directly to the deep bilge. The pan beneath the engine is one of those areas where water gets "dammed up", but my understanding is that this is to prevent oil and/or fuel, which may also be present here, from being pumped overboard by the bilge pump. I tend to accumulate small amounts of water underneath my engine, mostly from checking the flow on the Kingston valve before starting. There may be a little bit coming from the stuffing box, too.As for the advice that heeling tends to uncover hidden water, I can attest to that. On my boat, I've concluded that it must come from the water under the engine that spills over the rib that retains it, and then gets into the next section of the bilge, which does not drain anywhere by itself. My solution has been to keep the area under the engine as water-free as possible.