I really haven't found that that be the case at all with package management on OS X. Homebrew is almost always a joy to use, and on the few occasions I've had build errors using it I've found the Homebrew community connected to the official GitHub repo issues page to be one of the most responsive, friendly, and genuinely helpful open-source communities I've ever encountered. I agree things were a lot rockier back when the only package management choices were MacPorts or Fink, but Homebrew's a monumental step forward.

I can't say I've really touched Python at all, but as a relative newcomer to the Ruby world I found getting RVM set up and functioning properly on my Mac to be a complete non-issue.