I've been reading some teacher blogs, primilary http://moixland.com/ where he brags on Free, Open Source programs. Oddly, the longer I teach and the more I do my own design work, the more I value the ability to pick up the phone, or better yet, drop an email and get tech support.
Even goes back to my migration from MovableType to TypePad. Having constant reminders that I needed to update MovableType was causing writer block.
Another example is Lanschool. I love Lanschool and have used it over 16 years. Seriously. Hey, I've even met the developer/CEO of the company. Over the years, I've had few problems but when I do, those problems have become enhancements to the software. I pay for the legal upgrade every chance I get. AND I pressure my district to buy it too.
Why? First, I love the fact that I can drop them an email and get an answer by the day. I love the fact that I don't have to figure out the problem.
And as I tell my students when they are frustrated with free software -- you DO get what you pay for. Which reminds me, I'm about to pay for a maintenance contract on SnagIt and Camestia.