LaTeX. The tooling is awful, the error messages are close to useless, and any moderately complex document needs hacks and workarounds to accommodate the various

LaTeX. The tooling is awful, the error messages are close to useless, and any moderately complex document needs hacks and workarounds to accommodate the various quirks it has accumulated. I remember reading online somewhere "the best use of a 1 million dollar grant today to advance physics and math would be to redesign and develop LaTeX from scratch. The amount of productivity lost fighting against it is enormous." (Probably heavily paraphrased, since I don't remember the source.) Dr. Christoph Schiller, creator of the "Motion Mountain" physics book done entirely in LaTeX, mentions some of its other shortcomings here: http://www.motionmountain.net/onlatex.html http://www.motionmountain.net/onlatex.html