Xcode, GCC, and Homebrew 14 years ago
IAWTC. I'm on the fence about making the move from OS X to Linux. I've spent far too much time fighting unnecessarily complicated issues like this in the Mac environment. GCC issues. Lion Segfaults. MacPorts. Homebrew. Headaches.
Almost all of the tools I need I can install in minutes in Debian with apt-get. It's reliable, easy and gets me doing work instead of crying while I open 20 tabs trying to find solutions to obscure bugs on Google.