The best guess I can offer is that the buck needs to be passed on to an heir at least once. I noticed that brand new characters can never begin with 80 honor, even though 80 land, generalship, or kenjutsu are all possible. Honor can start at 70 at most. There is probably a link there. For kicks I backed up my save and set all the values to FF before winning, and got to see the 300-year shogunate message.
On the record, this game is the only abandonware I ever started from scratch, having never played it during its release. It's an awesome game.
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