So I got the Westsail’s rudder bearing housing glued in permanently. Picture here shows it in place with the bearing and cap removed for illustration. The housing has sideways and aft reinforcement along the axes of the rudder post. Those reinforcing webs are 1/4 inch G10 fiberglass sheet, doubled to 1/2 inch. It is the same material as the bearing housing (just a different color). The G10 sheet stock is really tough (it is actually FR10, a fire resistant version of G10). A 36 grit green grinding pad barely scratched it up. The pad would wear out and start smoking from the friction before I could get some good tooth on those pieces.
The final installation will see fiberglass and epoxy further attaching the housing to the hull in a method that will help spread side-loading forces from the rudder, to the hull.
As mentioned before, the bearing housing is designed such that, should the bearing ever need replacement (hopefully never), removing it would only require cutting the cap off (thereby destroying it) and sliding the bearing out. A new cap will need to replace the old one.