Having a difficult time picturing exactly what you mean when you say you have "a leak under the aft end of the prop seal".
Is it the hose coming off the
thru hull going to the stuffing box that is leaking? (If not, could you show us a pic of the leak). If it is the rubber hose, would take it apart during a
haul out and inspect the
thru hull and hose. This hose is typically a small section of
exhaust hose and would replace it. It is more of a pita to do this and why the PO probably put a tube of caulk on it instead of doing it correctly.
In general, you will need to uncouple the shaft from the
motor, remove the coupler, then push the shaft back enough to slide the stuffing box and hose off the forward end of the shaft. Measure the thru
hull carefully to
purchase the correct size rubber
exhaust hose. Can change the stuffing box packing and replace the hose clamps w/good quality SS clamps at this time also.
While you are at it, you may as well change the cutlass bearing and then you are done for a while.