I guess the plan is therefore:
1 - Get to grips with Fink on the Mac. (I am already happy with the basics of apt-get from using Debian GNU/Linux).
2 - Install Gentoo on a PC and get the hang of that, especially portage.
3 - Install the Apple Developer Tools on the Mac (they're on the second OS X install CD, I believe).
4 - Give Gentoo MacOS a try.