I did it on my 89 H28
Zen,I replaced the packing on my Hunter 28 2 years ago. It was alot easier than I imagined. I used a corkscrew-like pick I got at West Marine; however, when I unscrewed the packing nut, I found there was none of the old packing left, so didn't need the corkscrew after all.I made sure my bilge pump was working, and after unscrewing the nut I just allowed the trickle of water coming in to go into the bilge while I put in the new packing. I cut the packing pieces before I got started and angled the cuts as Steve mentioned. The flow of water entering around the shaft was pretty small, much less than I envisioned. The job was definitely doable while the boat was in the water.Good luck.