Paul:
First off, spray that all with WD40 and use a wire brush to clean up all that rust. Try to get that back to clean and shiny. Then you might be able to have a mechanic simply tighten the packing nut. The small nut on the bottom needs loosen then the large cap nut, the packing nut, could be tightened down mayb 1/8 to 1/4 turn and that may stop the leak.
If not, then, this all unthreads and that large packing nut slides up the rudder post. The packing material many of us use is GFO Gortex packing. You would use dental picks and remove the old packing and install 2 or 3 new rings of new packing.
With all that said, in 20 years, I have never had to repack our rudder post.
I would
#1. Clean it
#2. Tighten it.
This is the GFO Gortex packing
www.emarineinc.com/categories/GFO-Marine-Shaft-Packing
Hayden...off St Thiomas USVI