I agree that Iain M. Banks's Culture novels show that Stross's goal is at least possible. He did a brilliant job of imagining a distant future that gave me severe culture shock, but was also entertaining and engaging. Books set thousands of years in the future where we have the same viewpoints and aspirations do indeed make it difficult for me to suspend disbelief.
William Gibson's recent "Peripheral" provides two more near-term futures, both of which I would expect Stross to approve - the first perhaps two or three decades ahead that's a (perhaps appropriately) cynical view of the direction our civilizations are going, and the second perhaps a century on from that. With the closer one I could see where it was all coming from, and with the second the protagonist was able to relate better than I was... but then she was a couple of decades closer to it. It seemed to me a real tour de force. Recommended.
Looking back, though, I like to see how various authors did predicting their future in which we currently live. Heinlein's "The Door Into Summer" is still one of my favorites, but didn't work as a crystal ball. One of the Lazarus Long books placed his sidekick and tame math genius Andrew Libby on the spaceship's bridge using his slide rule to work his calculations. Gibson's 1984 "Neuromancer" hasn't held up very well either in this regard.
But Vernor Vinge's groundbreaking 1981 "True Names" still seems spot on to me, except perhaps underestimating the bandwidth that was going to be available. Anonymous hackers mostly stayed ahead of the governments, and Vinge foresaw some of our current network-based threats only a few years after the ARPAnet started spreading out from the universities. Like the protagonist Mr. Slippery, I feel impaired when I'm on a cruise ship with limited bandwidth and can't get instant answers to fleeting questions -- it seems that I'm not as effective a problem solver when I'm unplugged from the Net. Vinge even predicted the role of Homeland Security, though he had the Welfare Department cast in that role: when confronted by the authorities, Roger Pollack said "I do know my rights. You FBI types must identify yourselves, give me a phone call, and--". The response was "Perhaps that would be true, if we were the FBI or if you were not the scum you are. But this is a Welfare Department bust, Pollack, and you are suspected--putting it kindly--of interference with the instrumentalities of National and individual survival." And it keeps getting better. Pardon me, time to go read it yet again.