This pops up on slashdot every couple of months. Let me outline the reasons this is difficult from the perspective of one school. It sounds like you're trying to push forward an unfunded mandate. You're going to get a lot of pushback once people realize what you're trying to do.
- Apps. Educational software is often poorly written, and is written for mac and windows, not linux. One of the k-12 schools I work with has 350 applications, perhaps 330 which would have to be replaced under your plan. The K-5 students don't use openoffice, they use Reader Rabbit, there is no OSS substitute, and forget about making it work under wine. 6-12 use some generic office type apps, but also educational software. Keep in mind that entire curriculum and courses are sometimes tied to an app. You're not just replacing an app, you're asking teachers to re-write their curriculum. We're not just talking about typing software, we need software that keeps track of students performance and can run reports showing progress, comparing classes, etc...
- Hardware. IT budgets in schools are often small. You can get E-Rate money for some servers and network gear, but printers, digital cams, etc... are often old. Will your hardware work with Linux? What about the hardware your teachers use without your knowledge. Can you afford to replace it? If you replace old printers, you'll end up throwing away all your stock of ink, plus the ink you didn't know the teachers were hoarding. Some hardware is directly tied to an app for a class, you'll have to throw it away, you run into the same curriculum issues as with the software.
- Support. You'll need to support it. This means replacing or training your existing (unionized) staff. My experience is that schools typically employee underqualified staff. Clicking on things is rough, editing text files is really rough. If the staff can't handle the new tasks, can you replace them? This is a union and politics problem, and not an easy one.
- Training. You need to retrain teachers and staff. You'll again run into union issues, teachers are only required to do x hours of professional development per year, they simply won't take training classes, no matter how easy you make it. Keep in mind that teachers are continually asked to do more work with the same or less time/money, and you'll be asking them to relearn to do things. You might not be making any friends here.
Here how this does work, it'll take a few years...
First, do your TCO studies, show how there are no licensing issues. Licensing is a huge headache, solving that issue will win you friends it makes rolling out apps faster. Make sure the administration is onboard and working toward your goal. Doing all this is pointless if the superintendent comes back from a conference and decrees that everyone should have application X, which only works under Windows.
Modify your technology plan to require that any purchased software is web based and standards compliant. I've worked with "web based" apps that only work on IE, or require special plugins and etc... You'll end up losing a lot of functionality.
Take existing apps for which there are no good web based substitutes and see if they work with wine.
Roll out both of the above to one or two labs. Run them that way for at least a month. Make sure that your lab has an assigned lab aide, someone who takes ownership of the lab and is physically present when classes are using it. Keep on top of things, people probably won't report problems. When there are problems, solve them quickly.