One thing that you need to understand about me is that, despite appearances, I'm not a technology person interested in school reform, I'm a school reform person interested in technology. All of my professional training and most of my career within schools was aimed at progressive reform, with technology becoming the lever I am best able to wield toward that end.
Anyone who has been personally engaged in school reform, particularly public school reform, knows that it is not a game you win once and go home, it is an ongoing process, if not a war of attrition, and over a career you'll see many victories and losses, hopefully more of the former but don't count on it.
I also believe that the general purpose computer is a unique tool for learning, and while using computers does not inevitably lead to progressive school reform, it does grease the skids in many ways. Even measures which simply increase efficiency can free up time to focus on teaching and learning rather than paperwork and administrivia.
If you put those two things together, I think you can see why I am dubious of the current model of coupling a big, expensive technology rollout with a simultaneous goal of making comprehensive school reform happen, fast. That's trying to do two hard things (and the technology is the easier one) at the same time. The technology compliments the pedagogical reform, but it also puts even more political pressure on it, because it increases the cost in a very specific and high profile way, and as a result we see cases like this, where you spend a huge amount of money and political capital and get literally nothing in the end. No new technology or pedagogy.
If you want to do progressive school reform, you don't need more computers to start the process. I think you're better off making that move using what you've got on hand, focusing on teaching and learning, and if you get things moving in the right direction, the utility of technology to your teachers will become clear. They'll be chomping at the bit to start publishing online instead of little xeroxed booklets, turning those bulky binders into digital portfolios, running simulations of processes in science (and social science), etc.
But if you've already got a stable, sustainable, flexible (free!) IT infrastructure already in place, so much the better, even if when you start it is just being used for on-line quizzes and downloading porn. You don't have to go get a million dollar bond issue; you just need some new (free!) software and better administration, and you can focus your energy on teaching and learning.
In a sense, I'm asking for systems that fail more gracefully. Jim Heynderickx rightly points out that the 1-to-1 deployment that was the focus of the Times article last week was fraught with internal political divisions from the start, which led in large part to its failure. But on the other hand, does this mean that big technology deployments only work when there is political harmony? If so, we will never see them in the Providence Public Schools, even The Singularity won't change that. And I would argue that the political fighting around that technology deployment is inseparable from its cost. Cheaper technology means less political pressure and a longer timeframe for change.
We need sustainable, appropriate, free computing in schools, before, during and (unfortunately, often) after each successive push for progressive reform.