Well, after 23 hours uptime, submitting several problem reports over gettext, and a heck of a lot of compiling, it seems that my laptops updating is finally complete... except for a few stubborn packages that I rarely use anyway lol.
The thing that *really* pissed me off, is portmaster. Three times (gettext, gtk20, gstreamer-plugins) I had to manually do make reinstalls in order to get the freaking packages to install correctly. However portmaster saw fit to work it's magic, it forgot to install essential things, like msgfmt, libgstpbutils-.*, and and the actual gtk-x11 library \o/. Which obviously caused other ports depending on them to pop corks during portmasters updating them.
I think I'm going to again ditch the third party updating tools, flip the bird, and go back to using my own custom updater script. All that's really needed, is implementing the topological sort over dependencies anyway... then it would be automated in essence. And it's never doubled my work load the way portmaster and portupgrade do!!!