I use an iMac Duo and I have compiled python from source with no trouble, I have also used "MacPython 2.4.1" and "TigerPython24Fix" from http://undefined.org/python/ I install TurboGears from SVN and thus far have had no problems. I have never bothered using python 2.3. It's easy enough to upgrade - I have never used Fink (I did use darwin port (http://darwinports.opendarwin.org) for a short time but I prefer to compile, so I know what is where.)
If you have any problems, let me know.
