Hopefully that helps answer some of your questions.  Overall, I find the
FreeBSD ports system to be more flexible, but an acceptable runner-up
for purposes of binary package-based OSes in my opinion is Debian.

Just to add my .02$ to this topic, speaking from a perspective of a
FreeBSD lover in a company which prefers Debian, I must say that, even
though I administer a couple of FreeBSD boxes, I sometimes envy my
fellow Debian admins who manage tens of Debian boxes with a really
quick apt-get upgrade (or whatever the command) to fix a hole or apply
a patch vs. updating the source tree and making world on FreeBSD (not
to mention mergemaster which is a nightmare and the build process
which lasts for hours if not days). I'm quite frightened by the effort
I would have to invest to get the same effect administering a large
number of FreeBSD boxes.

Mind you, I'm not actually talking about the ports tree; given one of
the portupgrade/portmanager/portmaster tools, I usually find my way
through upgrading ports via source to be rather simple. On the other
hand, on Debian there is a price for simplicity, stable still ships
with really old 3rd party apps like Mysql 4.0, Apache 1.3, PHP 4.3...

To conclude my rantings, I really appreciate the effort behind binary
updates and freebsd-update project. Colin is doing a great job and by
using portsnap and/or freebsd-update, FreeBSD is slowly overcoming the
complicated upgrade process which combined with good ports tree and
above mentioned portupgrading toolset and portaudit makes for an
outstanding OS.

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