Yes, MS offers discounted versions of Windows and Office, but they're not cheap enough when competing with free alternatives, and many times not include all the functionality you want the users to learn (or there is a pirated old version available w/o DRM restrictions and enough functionality, which might be obsolete, but gets the job done, but also means that the student is not really being trained in a current product, so MS loses in both fronts: no license purchased, and the user won't promote its products when he/she becomes an employee of a company that can afford it). Also, prices didn't use to be as affordable as they're are now. If I remember correctly (it's been a while), the savings use to be in the 10% to 20% range, and there wasn't that much of a distinction between the commercial and academic version. Now the academic version is heavily discounted (seems about 50% or more) and you get extras like Encarta and other resources, but it might be too little too late.
And in their rush to make "affordable" editions of Windows and Office, MS has fragmented it and made it too confusing (to the point that users don't know what they need or have). Before, you had Windows and Office, and you pretty much knew the capabilities of your setup, and knew that you had everything you needed, you just had to click around the help files and figure it out. It makes sense to have up to 2 editions (maybe 3 stretching it), with minimal differences between them (ie advanced features, not complete applications missing). You could go for the low end to economize, knowing you could unlock more features, but now with all the editions and variations, you can't tell what you have. And then they introduce competing apps and suites (Outlook Express vs Outlook, and Works vs Office), further fragmenting the name.
You have corporate users doing diagrams in Excel or doing graphics designs in Powerpoint (instead of using Visio o Publisher), partly because of ignorance (ie, not knowing that there is a better program for that), and because the more suited application is not included with their edition of office, or what is worse, because someone in their team actually put thought into it, and opted to use the less optimal app in order to make it easier to distribute the documents even when their team had the budget for the full Office Suite (or their IT could install an Office viewer for the unsupported format). Instead of making it easier, it is just more complexity.
Maybe if MS were to give away started editions, with more features (maybe also forego activation on starter editions, and on older versions - if a user is stuck with XP or Office XP, let them, not even bother them with activation, even offer the old version for free on the web site). Getting students and home users hooked on an old version is better (for MS) than letting them go to a free alternative on another OS.
I don't really have a solution for MS: it just might be too late. The Vista debacle (and other MS missteps, like repeatedly failing with Tablets and Phones) and Apple and Google push for moving everything tot he network have cut short MS window to remain relevant by years (decades?). It's only option now is to hit a home run with Windows 8, and maybe remain relevant for a few more years, but it will be difficult to regain momentum. In a best case scenario, it might actually get what it wants: with thin clients (and W8 on arm), and most everybody will end up running its apps remotely (using RDP RemoteApp) on the cloud, and it will be sure that most anybody running its SW will be a legal user (since its on the cloud, there will be a stronger control on illegal copies). However, it will still only have a shrinking user base, with more and more users opting for less restricting options w/o DRM being recommended by their younger relatives or newly hired coworkers.