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
$HOME. 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. Note: I liked this setup, so I'm just curious and thought I inquire the hive mind.
I guess it depends on your needs. Personally, I use the latest version for any series (2.5, 2.6, etc.) from MacPorts.
I compile it myself because this gives me the newest 64-bit version. The official OS X builds seem to be 32-bit only. I dropped MacPorts several months ago because its dependency system and its often outdated packages were too annoying.
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