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It probably is easiest to do what @William suggests in his answer. Most people seem to have best experience with system python: http://answers.ros.org/question/110671/recommended-python-version-on-os-x-with-homebrew/. That being said, I have had success with the brewed python so far, but only after patching the cmake findlibpython module (and that patch is far from perfect as it stands).

Specifically your issue about sip looks like it might have been caused by switching to system python. After you switched to system python, the upgrade caused a reinstall, but maybe it was only accidental that there was an update at the time. As @William notes, among other things you need to reinstall (or uninstall and use rosdep to reinstall dependencies) all formulae with python bindings. He lists a few, a few noteable other ones are wxwidgets, pygobject, opencv, vtk, boost, etc. Unfortunately there is no easy way to list all the installed formulae with python bindings. See https://github.com/Homebrew/homebrew/issues/27136 for a workaround. Note that you should remove the contents of the /usr/local/lib/python2.7/site-packages only before reinstalling the formulae with python bindings, as they get installed there.

Actually, I just had the thought that checking /usr/local/lib/python2.7/site-packages for symlinks into the Cellar should give you a list of installed formulae with python bindings. The other packages in that folder are likely installed through easy_install or pip or manually by you. I believe that with system python, pip packages will get installed into a different location (namely /Library/Python/2.7/site-packages or ~/Library/Python/2.7/lib/python/site-packages for the --user option). That's not a problem, just a note for you.

I also recommend reading https://github.com/Homebrew/homebrew/wiki/Homebrew-and-Python before you start. If any more concrete errors pop up, just upadte your question here.