When you pull the rudder, you are going to want to change things to allow access. A rudder post and packing gland aren't something to be hidden away out of sight. You need to maintain them periodically, and that requires access. Hard to suggest without seeing all of it, but I'd cut and install whatever was necessary to make access easy, otherwise you will be doing this again. Two rudders? then do the other side while you have the tools warmed up.
It looks like "they" but a SS nylock on the bronze all-thread. And it looks like, one of those was put on upside down. They are very likely to be 304SS rather than 316, as the latter are rare locally. While you are in there, I'd replace the nuts with bronze nuts, two of them if you need it to lock. Bronze nuts are available from McMaster.