I recommend Golden Frog's VyprVPN service. I get their basic service as part of my Giganews subscription. There are cheaper alternatives (their service as a standalone option starts at $15/month), but they now have 8 endpoints, 3 of which are in the US. I use them at home to access sites that limit access to people who aren't in the US as well as using the closest local service whenever I'm traveling and stuck with open wifi connections.
"FAST on Linux is fucking awesome" I'll have to share that with the rest of the support team.
Speaking purely as an individual, I wish Microsoft wouldn't have gone this way, although obviously it doesn't surprise me. On the bright side - for your organization at least - you've got another 8 years where we'll be supporting ESP 5.3, so you have a few years before you have to worry about finding another solution, or deciding that maybe running a few Windows servers wouldn't be too bad. Just saying.
Computers are wonderful tools, but for most subjects students learn at that point in their lives (middle/high school in the US), computers aren't necessary.
Think about the primary subjects - Math, Science, and Literature/Writing - where do you see the benefits in using computers? Obviously for English classes, having access to computers to type papers is handy, but it's hardly necessary. Computers can be used in math to help illustrate concepts, but you don't want the students using computers to do their work, otherwise they won't know how to do it without them. And much of science is math - again, not something you want students using computers for.