Tim
I had my stuffing box serviced by a friend. We did it in the water. Stuffed a rag on the shaft to limit the water inflow and worked as quickly as possible. Deep bilge and good pump at the ready. Went smoothly, even though my 70 year old buddy said in all his days he has never worked on a more confounded, difficult, misguided engineered stuffing box. I asked him if we had hauled the boat would it have been any better? He said no. A little dryer, but not any easier. I suspect it will end up being 2 cases of beer, not one, and may be a dinner. I had fun being the gofer, learning, and listening to some salty language.
We could not get wrenches on the nuts to turn them. Had to resort to a steel bar and pounding it against the edge of the nuts to loosen them. Old school, slow, but worked.
Do expect some drip from the stuffing box while the shaft is turning No drip means heat. Heat means potential damage to shaft. Damaged shaft = $$$$$.
Best luck.