The table shows a lot of outdated non-GPL software, such as vim. Besides that, for many UNIX utilities, they could start cherry-picking from FreeBSD, NetBSD or OpenBSD, and you know, maybe even adding the missing functionality.
I think the actual reason for staleness is that there is not enough motivation for Apple to upgrade UNIX utilities. Many UNIX-savvy users can live with the older versions (in fact, many utilities have less features, because they were the BSD-variants). And if something is really too old, people just install a newer version via Homebrew.
Besides that, Macs are only a small part of their revenue and only a subset of that revenue is provided by developers and people using OS X as a UNIX. Of the developers, probably a sizeable chunk uses OS X just for developing iOS apps.
Personally, I'd like to see them update the user land with utilities from the BSDs and contribute back. But that's probably not gonna happen. The time that Apple was mostly a user-friendly UNIX vendor are over. It's a consumer device company now.
I was only addressing the GPLv3 programs because that was the grandparent was addressing. For Yosemite, lot of the other software, with the notable exception of Vim, seems to be fairly close in version to what the current release is. OpenSSL is an outlier too, but that may very well be a case of the amount of API changes with OpenSSL 1 that didn't provide a clear benefit, but did create new openings for problems.
With Mavericks, the situation is a lot like any other Unix distribution. Unless you have a very good reason for it, you don't want to break working code during a (mostly-)automatic update. For example, RedHat shipped Python 2.6 as the default for many years after Python 2.7 was released -- using 2.7 would have broken user installations.
Personally, I'd like to see Apple volunteer with the efforts the BSDs are making to create good BSD-licensed alternatives to the GPL software that's shipped. However, as you briefly mentioned, a lot of the software has different quirks and design decisions that will cause code to break. BSD grep, for example, mostly Just Works, however, I had to switch back to GPL grep on my FreeBSD box because a few bits and pieces had changed enough to make things a hassle.
Cherry-picking the BSD ones is problematic for backwards compatibility without making significant alterations. Many gnu tools support options that their BSD variants do not and some have slight differences in behavior even when using BSD compatible flags.
The table shows a lot of outdated non-GPL software, such as vim. Besides that, for many UNIX utilities, they could start cherry-picking from FreeBSD, NetBSD or OpenBSD, and you know, maybe even adding the missing functionality.
I think the actual reason for staleness is that there is not enough motivation for Apple to upgrade UNIX utilities. Many UNIX-savvy users can live with the older versions (in fact, many utilities have less features, because they were the BSD-variants). And if something is really too old, people just install a newer version via Homebrew.
Besides that, Macs are only a small part of their revenue and only a subset of that revenue is provided by developers and people using OS X as a UNIX. Of the developers, probably a sizeable chunk uses OS X just for developing iOS apps.
Personally, I'd like to see them update the user land with utilities from the BSDs and contribute back. But that's probably not gonna happen. The time that Apple was mostly a user-friendly UNIX vendor are over. It's a consumer device company now.