Whilst the boat is on the hard, we decided to look into the leaking rudders and removed all rudder hardware.
It appears that the hole in the wooden box is larger than the hole in the hull and it seems that it was not cut with a hole saw but small holes were drilled next to each other to make the big hole.
Overall, the wood seems to be solid, however, the oversize hole needs to be addressed. My mechanic is suggesting waxing the packing tube, fitting it temporarily in place and filling the void with west systems epoxy in order to create an even hole which will require less Sika to bed.
The packing tube will then be removed and re-installed with the adequate sealer.
Any idea whether this will work or any suggestions for an alternative fix?
Photos look worse than in person and all the rust is due to the yard using steel bolts instead of SS bolts.