Getting back to where you started. The boat was designed with a well, so the designer put some thought into it for a reason. The outboard in a well will behave much more like an inboard and the shaft will be sufficiently in the water at all times which will aid in performance especially in heavy seas. The motor in the well is easier to reach than an outboard hung motor. An outboard hung motor sometimes will come out of the water in heavier seas or if too many crew are sitting on the bow - not a problem with a motor in a well. The downside to a well mounted motor is that you cannot tilt up the motor out of the water as someone else pointed out, hence more drag, but most likely it is not on a racing boat anyway, so drag isn't such a both for day sailors or cruising folks. Sometimes, depending on the boat and design and ventilation features, you have to keep the hatch open to the outboard well or it will be starved of oxygen and will kill. Security, as pointed out, is better with a well. Also, unfortunately, the new 4-strokes won't fit into the well designed for a 2 cycle outboard without modification. In regards to HP......because sailboats are displacement hulls, they will only go so fast. So putting a larger outboard on it does not add to efficiency. One more point on the well verses transom bracket......The outboard on the transom will move weight further outboard on the stern while the motor in the well will not be so heavy on the stern, which is a good thing from a performance perspective and fore and aft hull trim.