Flipping LaTeX. I hate it so much.
To be clear, I don't have any real problems with the software itself, rather the kinds of people who push for it and they way they use it. For those who have never heard of LaTeX, it is a document creation software package that is like if Python and Word had a baby. It's super powerful and can make routine document creation easy and can produce beautiful documents. The problem is that everyone learns Word and by the time they are in a professional setting they have a decade or more of experience under their belt. LaTeX is picking up steam - especially in grad schools - but it is nowhere near Word in popularity. That, plus the steep learning curve, means that it is very hard to adopt it as a document creator organization-wide.
What typically happens is someone or some small group within an organization will get it in their head that they have to use LaTeX. Then they announce they are going to use it and begin implementing it. What they invariably fail to understand is that while switching to LaTeX may be a smart tactical move, it's often a strategic failure.
Had they stopped to have a conversation about what the impacts of rolling out LaTeX would be or how they would go about it, they'd understand the problems it can cause. But, no, the kind of person who pushes for it isn't the kind of person to listen to arguments based on things that don't directly impact them.
So they roll it out, no one can use it and before long they give up and leave a trail of documents that have to then be ported back to Word to be usable.
Worst off, almost all of the reasons they give for switching to LaTeX are really about crappy document writers at their root and not about crappy document writing tools. LaTeX is not going to fix people being stupid and lazy. In fact it can make things worse because stupid and lazy people that are forced to use it are not going to learn it properly and will create a slew of horrible documents that would have been of much higher quality if they stuck to Word in the first place.
Ugh I'm to the point where anytime someone says 'Hey we should use LaTeX!', my immediate thought is, (condescending tone) 'Oh, so you went to grad school. Neat.'