IF you'll happen to try out a Linux distro, I'd heavily suggest trying out Gentoo, since you're familiar with Ports, you'll just _love_ Portage in Gentoo - basically it's Ports which can handle dependancies and has a lot of other very nice options.
Really, I'm not doing this as a Gentoo zealot, I really believe in freedom of choice. I just thought you might be interested in reading a thing or two about it, since you mention Ports' lack of dependancy-management.
linkies:
http://www.gentoo.orghttp://www.gentoo.org/doc/en/portage-user.xml
