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I believe it's a matter of how much weight you can get on the side of the hull. For your 15 I would assume at least four husky guys, or ladies. Think of a racing cat.
1) how do you flip a Whaler in the first place?...
Most likely by hitting a wake or wave at speed. And/or by taking enough water aboard to swamp. Whalers are "unsinkable" but can be very unstable and flip when swamped.