BigJer, As an owner (11 yrs) of an '84 h27, I understand your frustration. Non-'83/84 h27 owners don't seem to appreciate how shallow the bildge is on these boats. It may only be 3-4 inches deep - barely enough room for the float switch to swing up. The problem is not so much having water in the bildge, it is that when sailing with a 20-30 degree heel, that water is forced out and onto the floor and into the storage areas under the port and starbord settees. Tools were rusting, anything hitting to floor while sailing will probably get wet - a pain.
The Cause - My Yanmar owners manual recommends running the engine at full throttle atleast 5% of the time. That's about 3900 rpm. Cruising is about 2700-3000 rpm. At idle and even upto 2700, my drip rate is very tolerable, however when I go upto 3500-3900, the water starts running in. My prop is clean and balanced and I don't believe the prop shaft is bent, but I can't prove that. I have considered a dripless stuffing box, but I have serious reservations as to wether would work under these conditions. Also installation would involve either removing the engine or the rudder( to pull the shaft back enough).
So I have opted with regularly changing and adjusting a better quality shaft packing. Last year I bought the graphite packing sold at the store on this site. My Bildge has been almost dry for 6 months now.
Now your 'Big Guy" problem. The access to the shaft area is a real problem even for me -5'10 - 200. I could only get one arm in to reach the shaft packing and when working, my shoulder blocked the view - basically changing packing with my eyes closed and with one hand. So last year I removed the plywood bulkhead between the berth and the engine/stern area. See Pic. As originally built, this bulkhead is not load bearing and is one long piece (over 4 ' long). So I cut at the support and made 2 pieces. It is held in place with a few (5-6) wood screws and only took 30 mns to remove. Now with a smaller piece at the shaft area, I can remove easily to work in the area with both hands and eyes on. This would give you adequite space.
A few other recommendatons - get one of the packing extraction tool (sold here also)-the No. 1 small size is best for this. Looks like a corkscrew and really works fast. Recognize there will be 3 or 4 layers of old packing. Be sure to have new ones cut and lubricated before you start. Since we have a 1 inch shaft, I use the 1 inch chrome hand rail to measure (wrap around) then cut.
If you do remove that bulkhead, consider repacking the steering packing gland also. The packing (larger size that the shaft packing) on mine was completely gone and this was another source of water in the bildge (the h27 squats as rpm increases and the steering packing goes below the water line, allowing water in.) See Pic.
Hope all this helps.