You have a Pearson 28-2 with a stuffing box attached to the shaft log, with 10 lbs. of caulk around it.
Here is what the shaft log on a Pearson 28-1 looks like: SailNet Community - jameswilson29's Album: Winter repairs: replace stuffing box hose
(See photo 12 of 21).
It looks as if someone improperly addressed a mismatch between the shaft log and the stuffing box by caulking the area or tried to stop a leak from the shaft log with caulk.
I would pull the boat, disconnect the coupling from the transmission, remove the coupling from the propeller shaft, remove the stuffing box, pull the prop shaft, remove all the caulking and thoroughly examine the shaft log and your stuffing box.
A failure in that area can lead to a very fast sinking boat. Pearsons are generally well-built boats. I doubt a failure developed there from normal usage, vibration, friction or some other normal wear and tear. I would not be surprised to learn that some extreme lateral force was applied to the propeller shaft, either through an impact in the water or a fall on the hard, and one of the POs or a sloppy mechanic simply replaced the bent shaft and stuffing box instead of properly repairing the shaft log.