On Tiger, I used a custom python installation to evaluate newer versions and I did not have any problems with that^*. Now Snow Leopard is a little more up-to-date and by default ships with

$ ls /System/Library/Frameworks/Python.framework/Versions/
2.3    2.5    2.6    @Current

• What could be considered best practice? Using the python shipped with Mac OS X or a custom compiled version in, say $HOME.
• Are there any advantages/disadvantages using the one option over the other?

^{My setup was fairly simple so far and looked like this: Custom compiled Python in $HOME and a $PATH that would look into $HOME/bin first, and subsequently would use my private Python version. Also $PYTHONPATH pointed to this local installation. This way, I did not need to sudo–install packages - virtualenv took care of the rest.}