Thank you all again for the tips and insight! The wealth of knowledge from the group is truley invaluable. The job is complete, but definitly is not one that I care to do again for a long time....
Getting the packing out was the easy part. Interestingly, I found 4 rings of old packing, 1 flax and 3 gore. My guess is the last time it was packed the top ring of flax was missed. I also think the old packing was ~3\8" as it is was significantly smaller than the 1/2". How they got 4 rings in there was a mystery to me (more on that later) but being the smaller size would definitly help. Besides the age of the packing, that might also be another reason is was leaking.
At first (with the quadrant on) I was only able to get 1 ring of 1/2" packing in the nut. This meant the quadrant had to come off as many suggested. My concern with removing it was that the stainless bolts might be seized to the aluminum quadrant, but fortunately they came right out. With the packing nut off the shaft, I was able to get all 3 rings of 1/2" packing in the nut but really struggled with getting the threads to catch when reinstalling the nut. I started second guessing the packing size based on the old packing and difficulty of getting the nut to screw on so tried 3/8" packing. While it fit, it seemed too loose around the shaft unless you really cranked the nut down to expand the packing. If it wasnt for the forum, I might have left it like that but thought 1/2" was the way to go because of the tight seal and the multiple comments about how difficult it was to get 3 rings on, all things I experienced. Going back to the suggestions here, what finally worked was installing 2 rings and tightening them hard to compress. I then removed the nut and installed the 3rd ring which, with some pressure, was able to be screwed on.
Reinstalling the quadrant also tested my patience as the markings on the shaft I made were rubbed off by the packing going on and off. Long story short, using the eyeballs on my fingers I was able to put the quadrant back together to where the cables ran smoothly.
The whole job took about 7 hours, half in the dark and rain as we are splashing the boat tomorrow in Titusville. I will honestly say, this tested my patience but am glad it's done and thinking about sunnier days already. Thank you all again for the tips and tricks, I wouldn't have been able to complete this myself without it!