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Garris, I agree with you that it is hard to keep the drain plugs out and permit water to freely flood portions of the boat. I have never intentionally left the plug out on the starboard side to see what the water level would rise to but might do so some day. Of course the water level in the tunnel depends on the weight in the boat and the trim of the boat. My splash well drain is like yours, well below the water level, and I normally keep it plugged with a removable drain plug. As I recall, with our normal load, the water rises about a foot from the bottom of the well with drain plug removed. Even with 10 people aboard (and in salt water), I don't have an issue with water coming over the transom....remembering my fish well is always empty/dry. But if I were to salmon fish outside the Golden Gate, I am sure that drifting with stern to seas would result in waves broaching the transom. Too bad Whaler did not build a variant configuration with transom height for twins of 25" length. Offshore, Whaler Drive is clearly the best option.
Al