Very cool to see the process of making a rudder. Thank you for posting. I will probably need to do this maybe my next haul, and I'm not looking forward to the 2 way shipping to the west coast. Adding in the cost of time on the hard stand, it may be cheaper to have them supply the rudderpost, then I can have the rudder on hand and just do the swap in a day. We don't haul out for the winter here, so space and time in the yard is very expensive and to be avoided unless absolutely necessary.
I have never been able to keep the rudderpost from leaking, even with 3 turns of packing. I am wondering if it is worth engineering a fix. The issue I think is that because there is no upper bearing, the packing enlarges and gets loose very quickly. I have an idea that might be a simple fix, to replace the lower turn of packing with an HDPE or similar bearing. Similar to a cutlass bearing with slots for water to lubricate it. That would hold the rudderpost so it would be easier for the 2 remaining turns to seal.
I highly recommend switching to dyneema instead of the cable. I made the switch 600 miles offshore when the not very old and still checked out fine SS cable broke, and I am not going back. Dyneema doesn't suffer metal fatigue from rolling around sheaves that are undersized. It's easy to work with and cheaper. It should last longer without failing, and you should be able to see issues with it before failing that are not visible with steal. And if it does fail, it's cheap and easier to replace. The sheaves should be replaced at the same time, but the whole idler sheave assembly is probably rusted and needing replacement anyway.