Sure, sometimes. Can't say it's been an issue for me. I'm sure it's more or less frequent depending on which ports you favor and how far you drift from release. (And it goes without saying: open source, send patches, etc.)

To be fair, I've found fewer excuses to not stay current on the OS since freebsd-update. cvsup and building your own source worked fine, but it was a little tedious.

pkg has done the same for the ports tree. If you just need the tool on the box now, pkg install bash. If you care about how the tool is configured, cd /usr/ports/mail/postfix; make config-recursive && make install clean. It all just works, works well, and works well together.

There have been some threads on HN lately about the frustration of changing the UI for the sake of changing the UI. FreeBSD rarely surprises me. When it does, the documentation usually sets me straight. (Or a few minutes browsing <https://docs.freebsd.org/mail/>.)

I lived through a lot of This vs. That flame wars and I've learned to roll with whatever the choice is. At the end of the day, they're all just tools I use to do my job; I use whatever tools are in vogue. But as a professional user of tools, FreeBSD is a very well designed tool and I wish I got to use it more. It makes my job easy.