I'm hearing lots of carping, but not a lot of citerefs of SF stories set in the far future that do honestly depict the impact advanced technology would have on society, culture, etc. at least in a way Mr. Stross would expect it to. Any /.ers have any in mind?
Well, there's the classics - both "The Time Machine" and "Brave New World" deal with societies dramatically transformed by technology, and deal with the storytelling challenges by contriving to have a contemporary narrator arrive on the scene via plot device.
Then, Asimov's Elijah Bailey sequence is really about two societies divided by their preparedness to embrace particular technologies. In fact... a society of people that are repulsed by actual physical proximity but think nothing of exposing themselves online... sound familiar? :-)
More recently, someone has already mention Iain M. Banks and The Culture... although its interesting to note that most of the actual stories just used the post-scarcity Culture as a backdrop to Special Circumstances agents interfering with more 20th-century-or-earlier-like civilisations (including 1970s Earth in "State of the Art").
Greg Egan has had a good go at tackling posthumans: most of the characters in Diaspora are intelligent software, and the remaining flesh-and-blood communities have diversified so much that different groups find it hard to communicate.
However, a lot of the "failures" pick their anachronistic societies for good dramatic reasons, not through lack of thought: I'd say that the (new) Battlestar Galactica quite deliberately made their society look like 1980s earth with spaceships. Firefly wasn't really a prediction that we'd all be wearing wild west costumes and talking cowboy in 500 years time: but that piece of whimsy saved a whole shedload of exposition about the structure of that society (also, if you're colonising, not only can horses make more horses out of grass, you can eat them if you have to: try doing that with high-tech a fusion-powered locomotion unit).