As I understand it, portage keeps a database of files it installs and is already able to determine if a file has been modified since. I would prefer that when files are being copied into the directories listed in CONFIG_PROTECT, if I haven't changed the original file in any way, that particular file is overwritten automatically. In most cases where a config file hasn't been updated, it is either an example file or the defaults are fine. If I haven't changed these files I am likely to not care if they are overwritten. Of course thera are problem some situations where this wouldn't be advantageous, but I would like to see it added as a configuration option to portage.
We can't do this because it isn't 100% safe, but you can set a CONFIG_PROTECT_MASK="/etc/foo" variable to tell Portage to simply overwrite files in the /etc/foo directory.