[madmanslitany]

All I have to base my opinion on is some familiarity with Blackboard/CourseInfo and a few friendships with schoolteachers, but I think you would need to approach marketing to high schools and colleges differently. Most high schools, even fairly good ones, are going to have a dearth of technical knowledge present in the administrative staff, so lightweight is good. They need software that is as easy to set up as possible, and they need be assured that it's reliable--schoolteachers and administrators are deathly afraid of parents and lawsuits, and something that loses grades is anathema.

(And I second what mahmud said above; the accomplishments in your profile make my head spin)