Hello,
Where I work we are using Linux Ubuntu servers, with their associated Landscape service. This service enables us to be notified of security updates (kernel, packages), and to apply them in bulk or per server basis (we just do a snapshot of the servers first). Lastly, a Ubuntu LTS (Long Term Support) can stay for five years, while still receving security updates.
I really prefer OpenBSD for many reasons, above all security, randomness, encryption, and also the great pf. The whole OS sounds more structured and solid. However I would have a really hard time pushing OpenBSD where I work, because of the need to upgrade every year (at best) or every six months. The third party packages provider M:Tier provides system and packages security updates as packages, that can be applied from command line. It brings a lot of fresh air compared to the way we had to apply packages security updates (building applications from ports-stable). It costs per server the same than Landscape, but it still seems like you have to log in into each server (no centralised web interface), and their LTS is one year (because obviously OpenBSD does not support older versions). At the end, every year the servers would have either to be rebuilt from scratch, or to follow an upgrade procedure that seems inconvenient (I read the FAQ about the sysmerge and all, it does not sound easy/error free/quick).
Please note that it is just my uninformed opinion, I knew OpenBSD at version 3.x (don't remember which one), then give up at version 4.3 at work because of the ammount of work to do (Linux was more automated and required less maintenance once set up), and just jumped back on the BSD wagon lately at home with the 5.5-current. I am by no mean saying I am right, rather I'm trying to explain why I find difficult to push OpenBSD in a business environnement. I would be more than happy to be wrong
Any opinions, input, and arguments will be welcome !
Regards,
Guillaume.