I think the only thing you've mentioned that really applies to me are the Lord of the Rings movies. I have both theatrical and extended editions of both movies because, in my mind, they're different movies. Believe it or not, sometimes I would rather watch the theatrical version over the extended version.
If people have been waiting for a "super dooper boxed set" of The Matrix Trilogy, then they've been waiting an awfully long time to own the first movie. That was one of the first DVDs I owned. If it turns out they re-release it (actually, they announced a re-release once, but then canceled it. I'm sure they'll release it sometime), then I, for one, won't go out buying it. Incidentally, I don't think I'll be buying Reloaded or Revolutions anyway.
I buy DVDs for the film, not the special features. Don't get me wrong, I enjoy the special features, but I usually only watch them once and then forget about them. The exception to that are for audio commentaries.
Here are some DVDs I bought before special editions were released:
Memento
Monty Python and the Holy Grail
National Lampoon's Animal House
National Lampoon's Christmas Vacation
National Lampoon's Vacation
Pulp Fiction
There's Something About Mary
True Romance
The Usual Suspects
X-Men
I'm not going to be upgrading them anytime soon. So, I guess in answer to your original question. I'd rather own them now and not waste my time with the re-releases.
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