[wrycoder]

I don't think there are many who send €50/mo, kudos to you! Few of their corporate users give much back at all.

I used OpenBSD as my workstation a decade ago and also ran it on a firewall box. However, upgrading the system every six months is tedious: basically, you manually download the files, overwrite the kernel and userland core, and then do a three way merge of /etc. Plus there's a bit of manual work required to deleted unused files and account for moved files:

https://www.openbsd.org/faq/upgrade65.html

After that, you still have to upgrade the ports tree (which has gotten easier).

Note that skipping upgrades is not supported.

Security updates between the six month upgrades are handled by monitoring the security list and downloading and applying patches as instructed.

If you are running a bunch of identical servers professionally, it's not much of a burden, but it is if you are upgrading one workstation and a firewall box. I got tight on time and went back to Debian/apt.

Does anyone here know how to do this more efficiently?

(It is a really nice system, and the man pages are superb.)

[yjftsjthsd-h]

Somewhat like sibling comment, I'd be really tempted to put /home on its own filesystem, control/configure everything else with Ansible (or Chef or Puppet or [...]), and just do a fresh install every 6 months. For bonus points, automate the install part with an autoinstall file. Keep in mind, there's setup cost here; it's easy for me to say because I'm already controlling my system with Ansible, but if you're just getting started it's harder.

[gbmor]

Upgrades and errata have gotten much easier.

For example, running syspatch(8) automagically downloads and applies the errata patches.

To upgrade, just curl the new bsd.rd from a mirror, place it in /, reboot, and type `boot bsd.rd` at the boot prompt. Then follow the prompts. I do this on several VPSes via a VNC console. It doesn't take long at all.

Granted, for personal use, I've moved back to Debian as well.

[sirn]

In -current there’s sysupgrade(8) that handles the “download bsd.rd, boot bsd.rd, upgrade, sysmerge” steps automatically in an unattended manner.

[asveikau]

sysmerge has made the upgrade process a lot easier in the last several years. It was a lot more painful in the past.

[jammygit]

Is it easier or harder to just do a full reinstall and reconfigure it with a script (chef or something custom), while preserving your data directory?