So after getting stuck and putting this work aside, I decided to take a second stab at it after meeting up with another Ubuntu developer in real life, and doing additional research. Using the experimental gcc-4.3 branch of Gentoo Hardened as a base, I'm now making extremely good progress bootstrapping amd64-pie, and the results look promising thus far.
For those of us curious, bootstrapping the archive is a straightforward if time intensive project. Essentially the process requires three individual bootstraps, an inital one that you use to build debian package, a chroot from those package, and a final chroot that is the end result.
Right now I'm working on the first part of this bootstrap, which is from a Linux host (without Debian) to generating the inital bootstrap packages. It requires compiling each build-dep from source with the proper configuration arguements, then building the packages with dpkg-buildpackage -d, and installing it, until you have build the entire base system.
From there, you take the debs, place them in a repo, and debootstrap, and then rebuild again, which produces the final result debs. It's straightforward and fasicating work (if a little tedious)