I deal with the support issue in the lab by running the free OSes off of LiveCDs. It runs a bit slower, and you have to make sure work doesn't get saved to a RAM disk, but it gives some flexibility in programs without affecting the machines. It also allows me to run apps that won't fit on the hard disks of our older PCs. Most of them are tapped out with XP and Office, it's all I can do to squeeze in a JDK and a framework for my high school classes. No room for The GIMP, OpenOffice/StarOffice, Pencil, a MUD, educational games, etc.
It also allows me to try adding new apps to my curriculum without doing installs on all the systems, and run a section on OSes in my computer classes that lets the students get some hands-on time with a variety of different OSes so that they learn enough to avoid freezing up if they're faced with an OS that isn't Windows.
As to the front office systems, I don't touch them myself. I've got enough trouble already.
Our systems are mostly old Dell desktops with some white label boxes and Fujitsu laptops thrown in. We have a few Intel iMacs that boot into either XP or OS X. Any of the systems will run Ubuntu 8.04, it's the only LiveCD distro we tested last fall that would run on everything in the lab (though the sound doesn't work on the aluminum iMac.) I also use Edubuntu 7.10 on all the old PCs--it's the last version of Edubuntu that comes as a LiveCD, newer ones come as an add-on disk for Ubuntu, which is no use without an install.
OpenSolaris runs on the Macs and some of the PCs, the non-Dell ones.
Dragonfly BSD runs on most of the older PCs, same with Knoppix and DSL. Puppy, surprisingly, has a hard time with our older hardware.
Anyway, if used well and in the right places, free OSes can work well. I haven't seen any open software for administration along the lines of, say, PowerSchool, that I'd be willing to use. There are projects, but not much in the way of results that I've seen.
Still, if you can extend the utility of some current systems to help the school put off buying new hardware for a while (assuming that buying new hardware is even possible), the free stuff can do that in the classroom.
You might want to look at my blog at
http://catsonkeyboards.blogspot.com/ for some of the experiences I've had with using free software in class. The "teaching" tags will pull the relevant articles.
Note: it
will cost prep time and class time, especially at first. If you have access to any students to use as guinea pigs outside normal class times for trial runs, I recommend starting this way.
I showed some of the teachers how to use the LiveCDs, too, but it didn't catch on until some of my students showed them how to do it in their classes. Once they saw a non-"rocket scientist" do it, they decided it might be something they can do, too. But when it was me demonstrating it, they balked. This year I'm just going to have a student run the demo while I stand nearby.
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