You know, I'd actually support a rather more abrupt transition, where we announce that on a particular date all digest files are going to be removed, thereby breaking any version of portage older than portage-x.y.z. Many people would probably miss such a deadline, but assuming that we also publicize how to download and unpack a portage rescue tarball then I would think that the actual pain would be minimal. (Indeed, we could even have a fix-portage.sh script in /usr/portage/scripts that would do the downloading and unpacking, if we wanted to be particularly nice.) Backwards compatibility is nice, but I'd really rather not see good ideas take a year to fully be implemented unless absolutely required.
How about instead of letting people use tarballs, we kill the digests for every package except portage and it's deps. That way we will break the system and enforce an upgrade, but we will also give them an easy upgrade route. (I haven't looked at the GLEP so I don't know about manifest compatibility).
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