Seen on pkgsrc-users@: A new tool for pkgsrc upgrades, called pkg_rolling-replace. It’s in pkgtools. It builds replacements for programs in order of dependency, without removing everything first. Strangely, it was funded by DARPA.

Also, the latest version of Apache 2.2 has been brought into pkgsrc.  I link to the message because it also describes how to set the 2.2 version as the default for every other package that requires Apache.