File systems on macOS are case insensitive. The system-provided directories are capitalized by convention, but you may also refer to them in lowercase if you like. It’s no more a “red flag” than `c:\WINDOWS` being capitalized.
I opt for the if-brackets rather than the one line syntax because it is clearer to read. “if this, then that” is less mental effort than remembering just how boolean operators short circuit, for me at least. It's a few extra lines but I prefer the layout, indent, and ease of scanning.
Windows now has optional case sensitivity on a per directory level. Drove me crazy trying to work out errors in an old c# codebase after a git checkout in wsl, multiple rounds of screaming THE FILES RIGHT THERE!
As of about five years ago, enabling that feature at mkfs time broke tons of apps that assume case insensitivity. Not sure if the situation has improved.
Speaking of filename weirdness.. I changed my Mac's language to Spanish a few years ago, as I was learning the language, which has many bizarre effects, online and off. One is that the Library folder in my home folder appears in Finder as Librería, yet if I try to cd to Librería or Libreria in bash it doesn't work, as it's actually Library. Same for Documentos, Imágenes, Aplicaciones, Escritorio (Desktop), Usuarios, Sistema etc. I haven't looked into how that actually works. But there seems something very wrong about files appearing as not what they're called, which I assume the whole non-English-speaking world puts up with.
Aren't you being a little over-dramatic? I use Uppercase directories (Documents, Downloads, Development) in my ~ as well, in a consistent manner. Why is that ugly?
I dislike CaMelcAse as well, but to each his own, I have stuff backed up from my windows machine on my BSD machine that has spaces and uppercase i leave it in case i need to restore. It does not mean you cannot take it seriously.
I actually do not own a Mac, but it is a decent OS and performs well and tries to be windows friendly (hence camelcase and spaces) and tries to be stable and secure.
Related fact: the term "case" dates back to the old printing presses where characters would be individual blocks or wood or metal and they were stored in draws. Capital letters were stored in the draw above non-capital letters -- hence why they are referred to as "upper case" and "lower case".
In terms of your general point, upper and lower case letters were originally different stylistic type-faces rather than "modes" of a letter in the same type-face. It wasn't until relatively recently in our writing history that the rules of capital letters became defined rather than a style choice and I'm certain they weren't thinking much about the problems that might cause with string matching on digital systems invented several hundred years later.
Offtopic, but this kind of one-line conditions are typically best written as
then it is easier tho change the sign of the condition (by using either || or &&)