The only really suspicious thing I see is that your shell PATH is *gigantic*. pulling things in from all over the place including Homebrew.  If you want to pursue further, suggest you try a clean build from the tarball without the modification and use a simple PATH like:

export PATH=/usr/local/bin:/usr/bin:/bin:/usr/sbin:/sbin

I'm willing to bet that some old versions of headers and/or libs are being picked up somewhere.  You probably should go through and permanently clean up that PATH.  Also make sure your Homebrew installation is up-to-date.  Rather than pulling in things from various places, consider pulling everything you need from Homebrew; it looks like you may have run various binary installers of various things in the past.  I'm going to close this issue.  Feel free to re-open if you discover something that appears to be a bug in Python.  Good luck!