The OSX package managers suck. I tried fink, macports, and homebrew. A lot of packages are simply broken especially now after Apple switched to clang. You end up in all kinds of weird situations. A friend of mine recently wanted to install Octave and gnuplot with homebrew and it took him several days until he gave up.
It's hard to get help with problems in OSX. This might have been improved. But back when I started using OSX in 2005/6 it was really bad. It was rare to find people with a good knowledge of the deeper layers of OSX. It was a complete different culture than Linux or even Windows. Maybe that has improved now that OSX is much more popular.
And it feels like Apple is more and more ignoring the UNIX folks.