Here's what I did to “shore up” the Woodruff Key slot. I cleaned the key slot, filed a slightly larger (non-metric) Woodruff Key down and used the Quick Steel epoxy putty to position the key back in the slot. All it took was a tiny ball of the epoxy to basically hold up the side of it. I let the Quick Steel dry for a day and sanded and cleaned the area very well. I also sanded the inside of the flywheel stub opening and test fitted it three or four times as you cannot see the Key once you put the nut on the crankshaft. I then coated the crank stub with a light smear of blue Locktite® to encourage the shaft to hold tight to the flywheel. I then dripped a tiny bit of oil on the slot in the flywheel to help the Key to slide in without binding.
When I was sure that I had it down by "feel" I cinched it down, bit-by-bit, by hand. I torqued it down to the spec 43 lbs. ft., hooked the stator back up, and put the shroud back on. I waited another day and gave it a few slow kicks with the plug out and the ignition off. I finally said "what the heck", put it together and kicked it over a couple of times for real. I let it idle and warm up fully before taking it on a little neighborhood ride. A quick stop at home for an idle adjustment and off I went, first to the gas station and then a couple of gentle laps around the neighborhood (within pushing distance). It felt good and ran pretty strongly. I parked it and let it cool before I re-torqued the flywheel nut, and yes, it had backed off a couple of lbs. ft. I added a few extra (close to 50) just to make sure that it knew that it was now one with the crank.
So far, so good. I've ridden it probably close to 45 miles with the Quick Steel solution in place. I'm going to monitor the torque of that crankshaft nut on a monthly basis just to be sure. Good times.