As a former teacher and now the Director of Technology for a school district in Kansas, I agree with many of these comments. I too am deeply involved in developing our technology and providing a "Differentiated" scheme to our school district Internet as well as providing additional training for the implementation of technology as a resource and not just another tool.
Our school district has a 1:1 laptop program with students in grades 7-12. The lower levels of students are about 1:1.5. Unfortunately, I too have to keep a CIPA qualified filter in place as our school district receives a large amount of funding through E-Rate to provide our Internet and Wide Area Network (WAN). So, Wesley is absolutely correct in his response to #3 Brett Moller. Unfortunately, this requirement is a federal stipulated law. Schools receiving E-Rate funding must meet CIPA filter regulation or face the government when they come in and audit the school district.
There is a large variety of filter options out there on the market. Some are capable of being installed and continue to work when a laptop is taken away from the school district. Also, many filters provide user authentication so each individual can be tracked in case of a violation. Then, based on the user authentication, one can provide different levels of Internet access. For example, we have certain teachers that have proved to be very capable of having an "Open" IP address. They too have to use the proxy server but have been provide a method that will remove those proxy settings when they need access to a specific site. Also, teachers in our district have the ability to request a website(s) to be opened. We ask that the teachers provide an overview of how the website will be used in their classroom. This documentation is recorded with the website information. The reason for this approach in opening a website is to provide proper documentation in case we are to be audited or questioned.
In closing, I do agree with some comments on Brett Moller's blog. Teachers do deserve the right to be trusted and students need to be able to earn/prove themselves. I make that exact same point when I meet with parents and students at the first of the school year in talking about Internet safety and proper usage. Those meetings are very interesting to listen to parents and their questions regarding Internet access. I am always amazed by how many parents are terrified by knowing their children have Internet access. Many of those same parents do not realize that their children can access the Internet from a neighbor's wireless AP.