"Predicting that self-driving cars would occur in ten years in the late 90s is pretty extraordinary"
There have been predictions of self-driving cars for more than half a century. It's in Disney's "Magic Highway" from 1958, for example. There was an episode of Nova from the 1980s showing CMU's work in making a self-driving van.
Researching now, Wikipedia claims: "In 1995, Dickmanns´ re-engineered autonomous S-Class Mercedes-Benz took a 1600 km trip from Munich in Bavaria to Copenhagen in Denmark and back, using saccadic computer vision and transputers to react in real time. The robot achieved speeds exceeding 175 km/h on the German Autobahn, with a mean time between human interventions of 9 km, or 95% autonomous driving. Again it drove in traffic, executing manoeuvres to pass other cars. Despite being a research system without emphasis on long distance reliability, it drove up to 158 km without human intervention."
You'll note that 1995 is before "the late 90s." It's not much of a jump to think that a working research system of 1995 could be turned into something production ready within 20 years. And you say "a year or two late", but how have you decided that something passes the test?
For example, Google Glass is the continuation of decades of research in augmented reality displays going back to the 1960s. I read about some of the research in the 1993 Communications of the ACM "Special issue on computer augmented environments."
Gibson said "The future is already here — it's just not very evenly distributed." I look at your statement of batting a thousand and can't help but wonder if that's because Kurzweil was batting a thousand when the books was written. It's no special trick to say that neat research projects of now will be commercial products in a decade or two.
Here's the list of 15 predictions for 2009 from "The Age of Spiritual Machines (1999)", copied from Wikipedia and with my commentary:
* Most books will be read on screens rather than paper -- still hasn't happened. In terms of published books, a Sept. 2012 article says "The overall growth of 89.1 per cent in digital sales went from from £77m to £145m, while physical book sales fell from £985m to £982m - and 3.8 per cent by volume from £260m to £251m." I'm using sales as a proxy for reads, and while e-books are generally cheaper than physical ones, there's a huge number of physical used books, and library books, which aren't on this list.
* Most text will be created using speech recognition technology. -- way entirely wrong (there's goes your 'batting 1000')
* Intelligent roads and driverless cars will be in use, mostly on highways. -- See above. This is little more common now than it was when the prediction was made.
* People use personal computers the size of rings, pins, credit cards and books. -- The "ring" must surely be an allusion to the JavaRing, which Jakob Nielsen had, and talked about, in 1998, so in that respect, these already existed when Kurzweil made the prediction. Tandy sold pocket computers during the 1980s. These were calculator-sized portable computers smaller than a book, and they even ran BASIC. So this prediction was true when it was made.
* Personal worn computers provide monitoring of body functions, automated identity and directions for navigation. -- Again, this was true when it was made. The JavaRing would do automated identity. The Benefon Esc! was the first "mobile phone and GPS navigator integrated in one product", and it came out in late 1999.
* Cables are disappearing. Computer peripheries use wireless communication. -- I'm mixed about this. I look around and see several USB cables and power chargers. Few wire their house for ethernet these days, but some do for gigabit. Wi-fi is a great thing, but the term Wi-Fi was "first used commercially in August 1999", so it's not like it was an amazing prediction. There are bluetooth mice and other peripherals, but there was also infra-red versions of the same a decade previous.
* People can talk to their computer to give commands. -- You mention Siri, but Macs have had built-in speech control since the 1990s, with PlainTalk. Looking now, it was first added in 1993, and is on every OS X installation. So this capability already existed when the prediction was made. That's to say nothing of assistive technologies like Dragon which did supported text commands in the 1990s.
* Computer displays built into eyeglasses for augmented reality are used. -- "are used" is such a wishy-washy term. Steve Mann has been using wearable computers (the EyeTap) since at least 1981. Originally it was quite large. By the late 1990s it was eyeglasses and a small device on the belt. It's no surprise that in 10 years there would be at least one person - Steve Mann - using a system where the computer was built into the eyeglasses. Which he does. A better prediction would have been "are used by over 100,000 people."
* Computers can recognize their owner's face from a picture or video. -- What's this supposed to mean? There was computer facial recognition already when the prediction was made.
* Three-dimensional chips are commonly used. -- No. Well, perhaps, depending on your definition of "3D." Says Wikipedia, "The semiconductor industry is pursuing this promising technology in many different forms, but it is not yet widely used; consequently, the definition is still somewhat fluid."
* Sound producing speakers are being replaced with very small chip-based devices that can place high resolution sound anywhere in three-dimensional space. -- No.
* A 1000 dollar pc can perform about a trillion calculations per second. -- This happened. This is also an extension based on Moore's law and so in some sense predicted a decade previous. PS3s came out in 2006 with a peak performance estimated at 2 teraflops, giving the hardware industry several years of buffer to achieve Kurzweil's goal.
* There is increasing interest in massively parallel neural nets, genetic algorithms and other forms of "chaotic" or complexity theory computing. -- Meh? The late 1990s, early 2000s were a hey-day for that field. Now it's quieted down. I know 'complexity'-based companies in town that went bust after the dot-com collapse cut out their funding.
* Research has been initiated on reverse engineering the brain through both destructive and non-invasive scans. -- Was already being done long before then, so I don't know what "initiated" means.
* Autonomous nanoengineered machines have been demonstrated and include their own computational controls. -- Ah-ha-ha-ha! Yes, Drexler's dream of a nanotech world. Hasn't happened. Still a long way from happening.
So several of these outright did not happen. Many of the rest were already true when they were made, so weren't really predictions. How do you draw the conclusion that these are impressive for their insight into what the future would bring?