My Experience
Even though I'd spent a lot of time on my O'Day 25, I had never done any maintenance on a bigger boat, so I had no experience with a stuffing box. I paid a guy to come do it for me while I watched. $60 an hour, with a four hour minimum (he did some other stuff for me too). It was money well-spent. The old stuffing was completely gone, and the compression nut was tightened down as tight as it could go. I probably would never have had enough confidence that I was "doing it right" had I tried it on my own, or may have even ended up slipping as described in here. I don't see anything wrong with those that jump right in and do it themselves (I'm usually like that myself), nor do I see anything wrong with taking the cautious route as I did. It's all a matter of what you're comfortable with.
Even though I'd spent a lot of time on my O'Day 25, I had never done any maintenance on a bigger boat, so I had no experience with a stuffing box. I paid a guy to come do it for me while I watched. $60 an hour, with a four hour minimum (he did some other stuff for me too). It was money well-spent. The old stuffing was completely gone, and the compression nut was tightened down as tight as it could go. I probably would never have had enough confidence that I was "doing it right" had I tried it on my own, or may have even ended up slipping as described in here. I don't see anything wrong with those that jump right in and do it themselves (I'm usually like that myself), nor do I see anything wrong with taking the cautious route as I did. It's all a matter of what you're comfortable with.