The teachers, though, *want* to be able to do this stuff. The fact is that the people who know tech in the district are either too busy fixing mundane things and managing accounts (they're sysadmins, not trainers) or they're overbooked. For a building with 150+ staff, we have one tech trainer that's in once a week, offering classes like "intro to microsoft word."
At the university level in the education degree programs, the classes still haven't been updated in probably eight or ten years. They're still requiring as the big, scary final project: a powerpoint with at least three images in it. Or, a newsletter that you assembled in Word with at least three images in it. The educational technology training at that level is a joke. There are generic blackboard trainings, but honestly blackboard's so bloated and buggy that it's been deemed by many of the staff that I work with to be too unreliable. I solved that by getting some cheap hosting and putting up a Drupal site that I've configured to pretty much mirror blackboard's capabilities (and even on shared hosting, it's more reliable than BB). That is far beyond the reach - even the conception - of most of the teachers I work with, not because they are stupid or luddites, but because they simply don't know the options. Not only that, the school's so sold on these huge packages - $10k a year for a flaky BB subscription and $400 Dell computers (old, slow, etc.) that they can't conceive of moving to an alternative.
Also, we use Pinnacle to enable communication between students, teachers, and their parents. Any parent or student can check grades & comments online. The problem is that most of the parents simply hate it, and the school can't go invest in a massive new package and try to move their data over. It's slow, it's flaky like BB (I've had all of my students unenrolled on a fluke, and it stayed that way for two days), and honestly, the students and parents just don't check it often enough for it to be an agent of change in parent/student behavior.
In summation: the tech they have sucks (it was sold to them by persuasive "consultants" - read, salespeople), and because they don't have access to decent training or resources, they don't know that tech can be an amazing ally in education.