So, after buying a round access cover of the right size, I made a masonite template and used a router to cut the exisitng hole to a larger diameter.
I discovered lots of rotten plywood as I went, which was predictable. After gouging out the rotton plywood and countersinking the bushing bolts into the deck and hand tightening them (the deck would compress
due to the rotten wood), I installed a temporary dam to keep the epoxy away from the rudder post, and replaced all the removed plywood with
West System epoxy mixed with strengthener.

I chose the access port such that the cutout size was smaller than the bushing bolt circle, and the finished edge covered the same bolts (mostly). The port was a very close vertical fit, as the finger indentations to open/close it had to be aligned carefully so they didn't rub against the rudder post.