Ross,
The fact you asked these questions, you have your answer.
If having to work on the shaft log & stuffing box, do it all the right way....do it once.
While you are at it, NOW is the time to go to a waterless shaft seal.
Green/fresh water belongs OUTSIDE the boat not inside. I've had mine for 15 years & it was worth the $225.00. No more dealing with drips & packing changes.
A friend I worked with talked me into getting a dripless buy stating,
"I NOW have dust in my bilge!"
CR