We started with Vernor Vinge's "A Fire Upon the Deep" in 1992. Tim Cain had gotten the CD-ROM version and it was the first ebook I read. Then we went back to the first Hugos and tried to read them in order. We had to go on scavenger hunts through used book stores to find some of the titles. I think we finished our book club with The Doomsday Book.
My biggest surprise was Rogue Moon (Hugo 1961). Incredible ending, up there with Man in the High Castle (Hugo 1963).
I agree with the "fascinating tour" part. The earlier books (from the 50s and 60s) where clearly more optimistic and more realistic at the same time. The human nature was captured more accurately I believe, most of the heros were actually anti-heroes. But the human capabilities were clearly over evaluated and the social interaction a little simplistic. Also, its funny to read books were martians were still a plausible thing (Protector Hugo 1973).
If I have an advice to give you it's: don't limit yourself to the 90s onward. You are missing on gems like Rendez-vous with Rama (Hugo 1974) or Forever War (Hugo 1976).
They would be flying around in their spaceships using slide rulers to calculate everything, wearing their fur-lined space suits etc.
But maybe you are right, it didn't get Hugo because it was too pessimistic, unfortunately, this one book gets more and more up to date with its predictions...
Just about at the end of Speaker for the Dead. A Canticle for Leibowitz was the first ones that I really enjoyed. Ender's Game and Speaker for the Dead are up there too but my absolute favorite so far is Dreamsnake.
I'm really annoyed at myself for not reviewing or at least jotting down some notes about the books as I've finished them. I remember liking Canticle a lot but I would be hard pressed to summarize it without some help.