Installing Fabric on OSX should be rather painless, but I ran into some problems related to PyCrypto when I recently tried getting it running on my Macbook Pro. PyCrypto kept failing with some missing libraries, and after a bit of investigation, I was able to find the cause.
I had recently upgraded Xcode in order to play around with MonoTouch. During the upgrade, I used the default options, one of which is to not install OSX 10.4 support. This apparently was what was causing the PyCrypto build to fail.
After reinstalling Xcode with 10.4 support, PyCrypto and Fabric built and installed fine.