Couldn't sleep again, so I decided I'd try one more time on the 2005.0 upgrade for Gentoo. Once again I just ran into walls where the emul-linux packages stopped doing anything once the script failed during the run. So I went a little nuts and started thrashing away at copying the missing pieces from the installation CD over to the live system. Got past a few of the errors, but the glibc build process still fails.
Guess I really am going to have to start over from scratch just to get this silly upgrade done. Urgh. PITA that.