Motor out
I've done it both ways, and find the easiest is to back my '74 C27 into my slip, and tie it up close so I have easy access to the outboard and transom opening from the dock. Then I disconnect everything, so the motor is just hanging loose on the mount, held by gravity. (I have a safety line tied to it from te sternrail, with a length so that if I happen to drop it, it will only fall as far as the powerhead being maybe 6"-8" ABOVE the water level. The fact that the line is attached to the sternrail means you can lift the motor all the way out off the transom and onto the dock while the safety line is attached. Then I get a buddy to act as the "guide" as a second pair of hands to be sure nothing gets tangled or hung up while my hands are full doing the "Incredible Hulk" thing, and I lift the motor out onto the dock. There is more danger in this way of dropping it in the drink, but it is much, much easier than trying to shoehorn it in/out of the lazarette hatch. Back in is just the reverse. My 15HP longshaft Johnson weighs about 75-80lbs - heavy for one person, but doable, as long as you don't have to move it far.