I concur with jggimi - "
always" is a dangerous word.
You care about your system, so
be sure that what you add to it is actually necessary or helpful to that system.
Examples in other parts of the IT industry:
- phone software
On my android phone I always see that there are updates to the apps that I have installed- when I see things like "added new platform availability" or other nonsense that doesn't apply to my usage, I skip it (in that instance it is obviously already running on my platform 
).
- network gear
If you work in the networking world and use Juniper, you'll notice that the JTAC will give recommendations on which version of JUNOS to install on your platform. It is almost always never the latest release. In the case of managing your OpenBSD systems, you are your own JTAC.
Do your homework, run a tight ship, and always keep your ear to the ground. Your system (
and maybe even those awful, awful users ) will thank you in terms of reliability and uptime, and hey, maybe even
performance.
It also doesn't hurt to ask questions here or on the mailing lists, as others may have reaped benefits or pain for something you are possibly considering.