I (I'm not the author) shamefully do some cargo cult Nginx because I don't understand how the location matching really works.
My ideal web server would have a configuration that resembles a decision procedure in a programming language, so I can have a mental model for what makes it choose one route over the others, and how settings are combined, etc.
Somehow Nginx repeatedly makes me and my coworkers very confused—are we crazy or just mildly incompetent? Should I read an Nginx book?
(One time I wanted to do something fairly straightforward, I think using a conditional inside some block, and when I looked in the manual it warned very strongly that this might cause segmentation faults. I was like WTF?)