[AtticusTheGreat]

There is definitely a lot to like about Homebrew (it's better than macports), but like others have said, when stuff goes wrong you can end up spending an entire day googling, only to end up going down a rabbit hole of archaic and often obsolete commands that may or may not work.

Once you get your environment set up it's fine, but try updating to the most recent Mac OS version with a ruby environment and you'll find pretty much all your gemsets broken in one way or another (if you have anything that needs native building).

I might just be bitter, though, as I spent most of a day working through this exact situation just last week.