While I won't argue with the rest of your analysis (You rule), I do disagree that it is harder to step and unstep a keel-stepped mast. Having stepped and unstepped a large number of masts, I strongly prefer keel-stepped masts, because you have better control over it, as soon as it is inside the boat. It is also faster to rig these because of that, as you dont have to worry too much about the standing rigging.
For smaller boats, like H-Boats its easier and faster with a deck-stepped mast, though.
Could be me
Originally Posted by Jeff_H
My biggest objections to keel stepped masts are to the purely practical. Keel stepped masts with internal halyards mean that there is always water in the bilge. This water comes in at halyard boxes and other openings in the mast and there really is nothing you can do will stop that. Second, it is way harder to step and un-step a keel-stepped mast making the boat more subject to damage in the process.