OK, I just made it back out to the tank ranch where all this stuff is located and I have to retract a few statements. The photo is a bit deceiving – it fooled me anyway-. I guess it’s the angle I took it from. Upon further inspection in person, the key does look like a Woodruff key and the flat side is facing outward like it’s supposed to. I think the deception was because the photo was end-on. Just at the top of the timing cam the crankshaft begins to taper and from the end view the taper cannot be appreciated. Therefore, it looked (to me) like the key slot was extending to the end of the shaft but that was not the case at all. Some of the slot was more visible than I expected because the tapering crankshaft exposes it. Sorry. The sideview makes it easier to see.
I also measured the length of the key above the timing cam at about 0.53 inches. The length of the keyway in the flywheel measured to about 01.92 inches, so most of the flywheel keyway is not engaged by the key. In fact, the length of the keyway that is visibly damaged corresponds pretty well to the 0.53 inches that is actually engaged by the key. That destroys my hope that the normal appearing keyway in the flywheel would somehow result in normal positioning and function of the flywheel on the crankshaft. Maybe time to look for another flywheel as Mumbles suggested.