Short bio: Computer Scientist, FOSS supporter (read more)
Tux Machines (TM)-specific
I don't have decades of experience supporting technology, but in the few years I've been at the academies I've noticed that several mistakes I've made were as a result of my failure to properly understand what I've come to refer to as the "Five Orders of Technology". The Order is a classification system of technology tools that has been, in my experience, a useful way of evaluating both potential purchases as well as existing technology and the ways to best support its use.
Technology tools at the top of the Order are the most preferred. They are tools that are both good AND predictable, meaning they accomplishes useful tasks with a high degree of quality while operating in a consistent and reliable manner. Examples would be a quality gigabit ethernet switch or an excellent industrial air conditioner.
The second order of technology are tools that are worth having, but just barely. They are bad, but operate predictably. They might be a network hub or Microsoft's Movie Maker. Neither one of these tools is particularly good at what it is built to do, but at least they both can be depended upon to accomplish what they do with consistency.
The third order of technology is a bit of a misnomer. It is to have no technology at all.