The utility pkg_add has a -u option that tells it to upgrade any existing matched package with a given binary package. Since pkg_radd passes options on to the underlying use of pkg_add, after automatically setting a remote repository for binary files, pkg_radd -u <packagename> tells pkg_add to automatically find and upgrade a package.
I never thought this would work. However, I’m building a package on a system that has pkgsrc-2010Q1 packages installed, but a pkgsrc-2010Q3 /usr/pkgsrc. Every time I’ve encountered an error because installed software was too low a version, pkg_radd -uv <package_name> has resulted in a quick upgrade.
I’m not recommending this as a new upgrade method; I’m noting how unexpectedly well this experiment is going. It may be just blind luck, but this sure would be nice if it ‘just worked’.