Kind of hesitant to drill through a brand new transom shield but what about the following alternatives?
1) Routinely shoot grease in from the inside transom plate to the swivel shaft area (not that much different from the nipple?)
or
2) If you are in saltwater, use fresh water to rinse the inside after each trip?
or
3) Spray something more liquid than grease after every trip from the inside like CorrosionX, Boeshield, Corrosion Block, etc...?
or
4) a combination of the above?
If you go to the link and scroll down to the housing cutaway you will see its impossable to get grease to the seal area..the corrosion you see is on a 2 year old housing