You're spot on - I caught a line in the prop about a year an half ago, which probably has something to do with this. (Although the gobs of caulk were there since I got the boat 10 years ago, perhaps concealing an earlier failure.)
I'm certainly haling out and dealing with this now - just trying to get a sense of the proper way to fix this, and also find out where to get the parts.
The arrangement on the 28-2 is very different than the 28-1, and resembles a thourg-hull, though that may be wishful thinking on my part
If anyone has an image of what it looks like outside the boat that would be tremendous!
I've already replaced the original stuffing box with a LasDrop Dry Seal a few years back, so am familiar with the process of removing the coupling, etc.
I don't know anything about the shaft log though, and it'd be great to find out more before starting the project (I'm using a mechanic but would still like to know as much as I can).