Apple just needs a better guy to be in front of this.
1. Those stupid IT guys only know what they learned on 1990's/2000's, an iPad is too complicated for them, I use the Apple's MDM software, it's easy to use, you can make what you want with an iPad it works well, and it's even free.
The thing is, not everybody is smart as me to figure it out. Most people working on IT management don't know what they are doing, and all they do is repeat the steps tought at formation.
Who formatted this guys? Microsoft, CISCO, etc. not Apple.
Collaborating with IBM here would be essential. Tim Cook, what are you waiting for?
2. Price. Apple, don't let Android or Chrome get into this, just give away the iPads at price of cost, right now. Inertia will bring you the $, it works for Microsoft, can work for iPad's in education.
3. Content, this one is harder, but it would help to make iBooks Author (ebooks that really look and do better than regular books) would help both convincing the teachers when they see it working. Also, a good strategy for lock-in.
4. Partner with logitech, they have an EXCELLENT keyboard for the iPad, it's expensive, tough. Offer a way that can charge both the keyboard and the iPad, and start manufacturing those things by the half million.