I agree with almost all your points. I honestly think some of the better films for Best Picture in 1985 weren't nominated - there are still a lot of people pissed that Brazil didn't get nominated, even though it won the LA Critics prize for Best Picture and Director. I'm actually not arguing the point on Africa that's actually considered one of the worst Best Picture winners ever and Weir was definitely a better choice that Sydney Pollack (Another Great talent but the Oscars gave it to him for the wrong film).
No disagreement for any of your choices on Best picture for 1989 over Driving Miss Daisy.
As to 1998, for whatever reason that year the Oscars decided that the only pictures worth nominating were either from World War II or Elizabethean era films. I agree with you not only for The Truman Show but just as much for Gods and Monsters. I'D say someobne will have to answer for Ian McKellen losing Best Actor to Roberto Benginii but I already know who that someone was, and we already know Harvey Weinsteim has more on his plate (I've actually written several articles about the Oscars that year, if you're curious.)
I was actually thinking of comparing Jewison to Weir. I once read a description online that Jewison was a director less famous than his films and in a different way that could certainly apply to Weir,