I recently repacked mine and found it pretty straight forward. First select the correct size packing, by measuring the diameter of the post, and checking w/ the mfg of the packing gland
for the correct size. I new mine was made by Edson
so I just referred to their catalog. Next wrap the packing around the post allowing for an overlap of the width pf the packing, cut both ends on an angle, I used approx a 30 degree cut overlapping each other, so when its compressed by the flange both ends will be pressed together producing a leak free surface. Apply packing lubricant to the post and gland, wrap packing around post amd tighten the bolts on the top of the gland until they are snug, but not any tighter than required to seal; you can adjust this latter... If the rudder
post is in a space restricted area (mine was) and you can only get one hand on it; you will need a helper, placing a tie wrap around the packing before tightning can help temporaily hold it in place until it is pressed in place, then remove.
Thats it....good luck