OpenBSD 6.2 came out a few days ago. An update on my new server was in
 order.

 I'm not comfortable with major upgrades on  BSD.  I  mean,  just  read
 their instructions:

 https://www.openbsd.org/faq/upgrade62.html

 Booting  a  special  install  kernel and what not, that's not what I'm
 used to. This is where rolling release distros like Arch are  so  much
 better.

 Good  thing  is,  OpenBSD  now has "syspatch" which can install binary
 updates during the lifetime of a release.

 So how did I upgrade from 6.1 to 6.2? I reinstalled from scratch.  But
 there are two important things to note:

   -- Virtualization

   -- Config management

 My  hosting  provider uses the same virtualization that I use at home:
 QEMU/KVM. This means I can set up a VM on my desktop PC, configure it,
 and  then upload it onto my VPS. It'll boot. The upload takes a while,
 but the actual downtime is just like two minutes. That's awesome.

 Config management does the rest of the job. It's  2017  now,  I  don't
 have  to edit files manually anymore. I use BundleWrap[1] to configure
 my server. (I still write all the  bundles  myself,  though,  to  have
 maximum  control  over  the  config  files -- and because there are no
 ready-to-use bundles for BundleWrap.) In other words, after I start my
 new  VM on my desktop PC, I do a "bw apply all", wait a moment, and be
 done.

 More work than with Arch Linux, though. With Arch,  you  install  once
 and then do a "pacman -Syu && reboot" once a month. Forever.

 ____________________

 1. http://bundlewrap.org/