I see no one has responded yet.
Can I suggest that you post on the "Ask All Sailors" forum? There is a much larger group that monitors over there.
Sorry, being from a use the boat all year climate, I can't really answer your question, other than mentioning that for me, hand cranking my Yanmar 2QM20 is really hard. Yes, I can use the hand crank to slowly position the shaft in the right spot for valve clearance adjustments etc, ... but certainly I wouldn't be able rotate it fast enough to get enough suction going through the oil pump. I've seen threads were people have asked about using the hand crank to actually emergency start a diesel. General experience is its very difficult, almost impossible to do. However, if you wedge open the decompression release lever, this will make hand cranking easier.
From my Seloc manual in the winter storage checklist section it says that after the other winterizing stuff is done, "7. Run the engine up to operating temp and then turn it off. 8. with the fuel shut-off pulled, squirt some oil into the inlet manifold and turn the engine over a few times without starting. This will spread oil around the cylinders and prevent rust and corrosion from forming."