Hi Here is my idea for dealing with the /usr/share/doc problem. Have a symlink in /usr/doc for each package which has moved to /usr/share/doc. The symlinks could be created by the postinst of each package (imho not a good idea), or dpkg could be modified to run scripts in /etc/post-dpkg-install.d after installing or upgrading packages. A /usr/doc compatability package would contain a script to create the symlinks. This would also work if dpkg was not upgraded, except the script would have to be run manually or from a cron job.
-- Rob Murray