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Re: How Low Can We Go? (hp)
Paul, bear in mind that if you cut up the transom or do some other "improvement" you will probably destroy the resale value of the boat. In case you don't plan to keep it forever, or give it away when you're done.
With something like an engine, it is impossible to drop it over the side unless you really want to drop it over the side. You buy some web strapping, or some stainless cable, and you attach it to the engine and the hull. Worst case is that you drop the engine, it gets submerged, and you pull it back onboard.
Probably the simplest solution is just to use the topping lift (if you have one) or rig something else so you can hoist the engine up and lay it down in the well or nearby, with it secured to the boat and with a mechanical advantage to make it easy.
When a boat is designed with a well (personally I call it a bastard design, I don't like them) that usually means the designer wanted to get the weight off the transom, and if that's what they wanted, and they went to the expense of a well do to that....I wouldn't be so eager to undo all that work.
If you just want the engine for docking or maneuvering in sheltered waters (i.e. Sheepshead Bay) probably anything will do. If you want to buck a five or six knot current with a 20-knot headwind against you...You might as well go for the lightest 9.9 that you can find, or something close to it. And it will still be easier to handle if you arrange to hoist it, because all it takes is one lurch from a passing wake, and you can easily throw your back out or drop any load--like an outboard.
If you have a spare main halyard, that makes a perfect extra lifting line.