The real problem with LaTeX is that it doesn't try to make itself friendly. It gives horrible errors that are big headaches for newcomers, and setting up your environment can be a pain. Early today, someone set me a document and I spent 15 minutes finding and updating the right packages until it built.
That is probably my biggest qualm with it, and really only problem I face. That there are a lot of libraries that do the same thing, but are incompatible. If there were standards it would solve a lot of problems.
