Django - Mac development, environment hell
Second, would it be easier to set up
  the entire environment on Ubuntu than
  it is on a Mac?

To answer this question (though I never used Mac though): I never had problems setting up a python environment for Django development on Ubuntu. Though in any case you should go with the built-in Python version if possible. Attempting to install any other Python versions usually ends up messy. Luckily with Ubuntu 11.04 the standard version is already 2.7.
I was trying to setup Django dev environment on Mac and arrived into a hell. It all started when trying to install PIL, which failed after trying 15 or so different recipes I found on blogs. So I wanted to install the Python, this time 2.7, and reinstall setuptools, easy_install, pip from scratch. 
After just installing Python 2.7, and easy_install with setuptools for 2.7, this all in turn created such a mess that is unbelievable. Different version of Python are installed everywhere, easy_install is installed everywhere and points randomly to different python hashbangs (sometimes to #!/usr/bin, #!/usr/local/, #!/Library/...)  
Now I can't even do easy_install pip, which I always could. So I'm already in a hell and I haven't even attempted to install MySQL yet.
My question finally is did anyone bump into such problems, it would help enough to know that I'm not alone. 
Second, would it be easier to set up the entire environment on Ubuntu than it is on a Mac? 
Thirdly, is there any guide that can really clearly explain how to set up but also tear down the stack for Python development on a Mac?