One point to check. If your boat is like my old one, if the shaft comes out of the coupling it can move backwards far enough to go through the shaft seal, flooding the boat. In fact in my boat the whole shaft and propeller could be lost that way, it happened to a sister boat. My solution to that potential problem was to fit a spare anode to the shaft just ahead of the shaft seal.
I have 12 inch lengths of woodruff steel; but if I was stuck I would get an angle grinder & a high tensile bolt & grind it square along its length. It does not have to fit perfectly. If it is slightly loose & the clamping force of the fitting does its job, it makes no difference. If the shaft does slip a few thou, then the bolt will bind. I cannot imagine it will shear, being HT & if it did it would be due to massive force & probably better it did shear.
Well - as Sod’s law would dictate - I found the key in the bilge while we were in the slings preparing to launch! At least I have the option to refit it now if I ever so desire.
I was happy with how it went together without. The 1/4unf (I think?) grub screw was reassuringly more beefy than I’d remembered and fitted the dimple well so I installed it in the end.
I’ll experiment and see if it moves at all (in what will necessarily be early ‘sea trials’ around the marina anyway). If the screw does damage the shaft, it will only be one more step towards its near demise (it and the prop are coming to the end of their 33 year life ?)