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Once free from the coupling, the shaft is free to move, and with me lying over the engine, head upside down this looks like it could be tough. I plan on bracing the shaft against the downward pressure of a drill so I don't torque the stuffing box & stern tube.
What I was thinking would help, is a tool I remember seeing that was just for drilling a hole in a cylinder. It was a clamp type thing that had a tube for a drill bit. It held the bit in center and perpendicular to the cylinder. Now, I can't remember where I've seen this or what it would be called. Google searches for "drilling holes in cylinder" doesn't help.
Anyone know what I'm talking about??