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How do you re-install the flywheel without knocking the key out each time? Do you install the key into the shaft first and then install the flywheel or do you install the key in the flywheel notch and then install the flywheel onto the shaft?
I have yet to find a decent trick to it. Its more a game of patience, and a precise placement. The woodruff key should be placed on the crankshaft when installing. At least that's my opinion, and how I do it.
You clean the flywheel keyway with a small file to remove any burrs or possible corrosion. You rub both sides of the key on fine sandpaper to again remove any burrs or deposits. insert the key into the crankshaft vertically. Do not match the taper of the crankshaft.
Stand on a stool so you are well above the engine and can look down. Line up the keyway in the flywheel hub and carefully put the flywheel down onto the crank.