I started building sites with Django in 2008 and it's a little crazy to look back and see the improvements and growth that Python and Django has experienced in that time. Remember trying to install everything with Macports? Environments were a beast to deal with. Then a few years ago Homebrew came along and its now pretty much the first thing I install on a new Mac to start setting up a local dev environment. If you haven't used Homebrew yet, you're missing out.
Give Homebrew a try today. You'll be glad you did.
Update: 5/22/2013 I also use fabric to automate deployments and other tasks. After installing it I found it saved the fab executable to a folder /usr/local/shared/ that wasn't on my path, so I couldn't run it. I fixed it by adding that to my path in ~/.bash_profile
It now looks like this:
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