[they4kman]

For complicated situations like this, nothing beats MacPorts. Where brew is generally based on recipes (read: collection of bash scripts) that may or may not play well together, MacPorts is a package system with well-defined dependencies. The drawback to MacPorts is that everything is built from source, and nothing previously installed on the system is utilized -- so installing Python for the first time may take 30-60 minutes. But the next time is 5 minutes, and you can install all the versions you want, where they'll live side-by-side in peace and love and harmony.

MacPorts is slower, but offers peace of mind -- 'cause when I'm trying to develop something, the last thing I want to worry about is dependency issues (gross)

[pseudalopex]

MacPorts has binary packages. Homebrew uses Ruby not bash. MacPorts uses Tcl. MacPorts just has better QA.

[cutler]

I don't understand. I've been using MacPorts for 16 years and I've never had to wait more than a few minutes for a Python install to complete. Most packages are pre-built. I can even get clang without having to compile. Plus one for MacPorts though. It rarely lets me down and unlike Homebrew stays in /opt/local instead of polluting /usr.

[icedchai]

I've seen MacPorts uses pre-built binaries, at least in some cases. Not sure if this applies to the Python ports.