rudder post leaking
I have the same problem. The boat squatting at the stern at hull speed would increase pressure at the nut making it leak more underway. Prop wash may also increase the pressure. The nut at the top of the rudder post housing is a packing nut and theoretically should be adjustable similar to the shaft stuffing box except it is insanely inacessible and perhaps frozen and rusted. Sam Lust has a number of postings earlier this year on the sinking hazard involved since the packing nut is very close to water level. He also outlines his replacement of the nut which he did with the fuel tank out of the boat.