I work for a school district and they have similar problems. I think there are
two things that encourage use of certain software over other software where I
work. One issue is that the people in charge tend to fall for a good sales
pitch. We're using an IBM product for one project because the company that sold
it promised the product would do everything we needed and be cheaper than other
rival commercial products. It didn't deliver, but the company that made the
product before IBM bought them was the only one that would promise that it would
do everything asked for. The other product dealers were more truthful and said
certain things couldn't be done and thus, their products weren't purchased. The
other factor is that they tend to like support. If a company promises to take
care of any issues (whether they do or not), that product is more likely to be
purchased. Also, if the people are already familiar with a product, they'll
tend to stick with that product, because they're comfortable with it. There's
definitely a safety factor involved. If something goes wrong, the technical
support people for the schools (who really aren't all technically trained) want
to make sure there's someone behind the product who will take care of the
issues.

It's really frustrating, because I could write software to do some tasks we need
or recommend Open Source software. We could save a lot of money. Instead, we
end up buying stuff and there ends up being a lot of hidden costs because the
products really don't live up to the hype. Then, we end up buying other
products or services to fill in the gaps or have to live with software that
doesn't quite do the job.

They also seem to like to go with what's popular. Our district just got a grant
and is buying a bunch of IPads with it, even though they're not compatible with
other software we're using in the district like our reporting systems.

Would love to see Linux developers/users offer more out-of-the-box solutions for
schools and publicize support options a lot more. There really are some good,
viable Open Source solutions out there. However, educating educators about them
and helping to give people confidence in using them is not easy.