[nelsonic]

How long did what take? Learning the essentials of OpenBSD, budget 4-6hours. Switching over servers from Ubuntu, an hour for the first one then 10mins each after that. You can copy config with your favourite tools; most have ports for OpenBSD already. If you want to learn more in-depth, read: Michael W. Lucas Absolute OpenBSD, 2nd Edition: Unix for the Practical Paranoid. Highly recommend it as teaches many fundamentals most software engineers skip.

[reidrac]

How many upgrades have you done so far? And how many kernel fixes?

Long time ago I maintained a couple of obsd servers, and the cost in time of upgrades and the (occasional) security fixes was substantial.

I still maintain a couple of servers, but if it wasn't because Debian makes it easier by automating most of it, I don't think I could do it.

Yet I miss my time with obsd. I'm very interested in your experience.

Edit: it was 3.6-STABLE. Things have changed since then.

[noAnswer]

They have binary updates by now. No more need to download the source from CVS and compile fixes.

You can update from one OS version to the next with manly only one command.

[miah_]

syspatch and sysupgrade have made things substantially easier these days.