Yes, those rubber bolt shank seals could be the culprit!
The main rope seal could also be the culprit!
The inside large rubber cushion ring could also be leaking!
The joint between the Y-pipe and shield could be leaking (there are six O-rings here)!
A soft transom could be allowing the washers to sink into the transom core, causing a loss of tightness between the transom shield and hull.
As you can see, there are several areas that could be causing this.
While this is NOT a proper fix, you could loosen and drive the carriage bolts AFT....., seal the carriage heads, drive them back FWD....., install a larger plate washer on each......, re-tighten the six nuts......., then clean and seal around the perimeter of the transom shield.
With the carriage heads sealed against the shield, this circumvents the task of the six rubber bolt shank seals.
Sealing around the perimenter of the shield circumvents the task of the large rope gasket.
Like said, this is NOT a proper fix, so think of it as temporary only!