While your article addresses specific examples, I feel that one of the biggest technology blunders as a whole has been using technology to fit needs we don't have as people.
Successful businesses that don't rely on previous marketshare or smoke and mirrors, provide services or products that make sense and fill a need.
I know, that's obvious, but when you look at a lot of the technology blunders mentioned, they violate this.
Technology developed to where we could move music around, and when it became available, instead of changing to what people wanted and were aware of, they fought it and tried to make money off of a failed business model. While it maybe made their numbers for a few more years, we all know these labels, without a dramatic change, will fail. If the suits at the labels don't know it, their kids sure do.
HDMI, like you said, is this all over: "It's also easy to see how high definition audio required, in theory at least, a new cable configuration and some additional copy protection to give the record labels the warm fuzzy of knowing that it would take an extra week to crack the revised standard for encryption... but I digress" ... couldn't have said it better.
Number 5 is the only one I kind of disagree with. I think that, while we as "Audioholics" feel that SACD and other improved formats would have been the obvious successor to CDs, with the rise of protable players sound quality took a back seat to portability. But this didn't violate the rule of giving people what they want, as a whole. Compressed music that sounds louder on an iPod, and smaller file sizes, were simply what people wanted. Now that memory is so cheap, and bandwidth to match, this might falter in the future.... but with the rise of digital came a fall for places to experience good sound. When I was a kid, lots of people had nice speakers and had pride in their equipment.... now people don't seem to even care.
As for Vista, I'm still in trouble with it. And I'm so stuck, that I find myself sitting here praying 7 will be better. While Mac and Linux have taken some of the marketshare, I agree that Me and Vista was the end of them. Because they are so big, it will take a while for them to fall, but they are already falling. I'm sitting here waiting for Linux, or anything better, to support for my software at work... Waiting. And its coming, I betcha.