When i got my H33 it had been an insurance hurricane write-off. The boat had bounced around on its rudder. The post comes up a sleeve and a stuffing box keeps the water from pouring in (theoretically). That sleeve is heavily glassed to the keelson and is supported near the top, laterally, by a fiberglass plate which extends to the hull sides where it is tabbed. My plate had torn away from its tabbing, allowing the rudder to flop over sideways. I suggest you check to see if that plate is securely bonded to the hull. If not, fix that first. If that plate is askew, it will cause the shaft to bind. Also, before dropping or raising the rudder, make sure the stuffing box on top is loose. (Incidentally, the nut which packs down the flax is notorious for corrosion and pitting. There were a number of posts about this quite a few years ago. I repaired mine with carbon fiber and epoxy, but then I am not in salt water.