Responding to some of your points:

I have a bit of an obsession with Citizen Kane. I understand why you're less keen on it, but I find it mesmerising and constantly see new things in it (I've watched it countless times).

I have a similar obsession with 2001, which I find utterly hypnotic. Again, I've seen it more times than I've had hot meals (five of those times in the cinema, including a 70mm print, which is really the best way to see it). I can't say I think of any of it as irrelevant (including the scene with the Soviets) but I get that it isn't everyone's cup of tea.

Completely agreed re: The Searchers, Vertigo, and that the Academy must have had it in for Hitchcock.

Jumping ahead to The Truman Show, I'm less keen on Shakespeare in Love with every subsequent viewing, but yes, most people lament that it beat Saving Private Ryan, not The Truman Show. My own take on this is that whilst Spielberg deserved the Best Director win (after all, that film proved hugely influential for the astonishing opening sequence alone), The Truman Show would have been my Best Picture choice, on points, as I think Saving Private Ryan isn't quite as good a film overall (though it's still a very fine piece of work). If The Truman Show is one of your favourites, you might enjoy the article I wrote on it, which I linked to in the article (if you haven't already read it). :)

Apocalypse Now is a flawed film, I grant you (including Brando's largely pretentious mumblings - he gave much better performances in the likes of A Streetcar Named Desire and On the Waterfront). However, somehow none of this matters in the end. I don't even think it matters which cut of the film one sees (with or without the French plantation). I still come away from it with the same absolute horror every time. It's so, so good.

By the way, I am not a fan of The Deer Hunter. It has a few powerful moments, but... well, to paraphrase one critic at the time, the wedding sequence went on so long, I was embarrassed that I didn't bring a present. :)