It probably depends on the boat, the conditions, and the mounting of the outboard... but we sail in waters that can get pretty choppy and I've seen many an outboard on various sailboats nearly get swamped while motoring...
I prefer the inboard diesel. If you are only racing the outboard out of the water has less drag. The diesel is much safer than gasoline and more dependable and ecomoical. An inboard diesel is definately worth the extra money in the resale and safety side.
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