I did some additional tests and reinstalling openssh-server does not
break it. It only breaks after the update procedure.

To recreate the error, take a fresh OpenVZ 6 Templates of Ubuntu 16.04 64bit, 
and simply do:
apt-get clean && apt-get autoclean && apt-get autoremove && apt-get update && 
apt-get upgrade && apt-get dist-upgrade && reboot

Maybe there is some other package than openssh-server that breaks things
down.

Here is some of the output of update procedure:
Setting up systemd (229-4ubuntu21.15) ...
addgroup: The group `systemd-journal' already exists as a system group. Exiting.
[/usr/lib/tmpfiles.d/var.conf:14] Duplicate line for path "/var/log", ignoring.
Failed to openat(/dev/simfs): Operation not permitted
Failed to validate path /var/run/screen: Too many levels of symbolic links
Failed to validate path /var/run/sshd: Too many levels of symbolic links
Failed to validate path /var/run/sudo: Too many levels of symbolic links
Failed to validate path /var/run/sudo/ts: Too many levels of symbolic links

...

Unpacking openssh-server (1:7.2p2-4ubuntu2.6) over (1:7.2p2-4ubuntu2.1) ...
Preparing to unpack .../openssh-client_1%3a7.2p2-4ubuntu2.6_amd64.deb ...

...

Setting up openssh-server (1:7.2p2-4ubuntu2.6) ...
locale: Cannot set LC_CTYPE to default locale: No such file or directory
locale: Cannot set LC_MESSAGES to default locale: No such file or directory
locale: Cannot set LC_ALL to default locale: No such file or directory
Failed to validate path /var/run/sshd: Too many levels of symbolic links

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You received this bug notification because you are a member of Ubuntu
Touch seeded packages, which is subscribed to openssh in Ubuntu.
https://bugs.launchpad.net/bugs/1814124

Title:
  sshd does not start after update

Status in openssh package in Ubuntu:
  Incomplete

Bug description:
  After processing system update by:
  apt-get clean && apt-get autoclean && apt-get autoremove && apt-get update && 
apt-get upgrade && apt-get dist-upgrade && reboot

  ssh server stops starting at system boot.

  It starts after doing:
  mkdir /var/run/sshd
  chmod 0755 /var/run/sshd
  service ssh start

  It happens on fresh Ubuntu-16.04 installs on every VPS provide I have
  tested so far.

  ProblemType: Bug
  DistroRelease: Ubuntu 16.04
  Package: openssh-server 1:7.2p2-4ubuntu2.6
  Uname: Linux 2.6.32-042stab127.2 x86_64
  ApportVersion: 2.20.1-0ubuntu2.18
  Architecture: amd64
  Date: Thu Jan 31 10:18:56 2019
  ProcEnviron:
   TERM=xterm
   PATH=(custom, no user)
  SSHDConfig: Error: command ['/usr/sbin/sshd', '-T'] failed with exit code 
255: Missing privilege separation directory: /var/run/sshd
  SourcePackage: openssh
  UpgradeStatus: No upgrade log present (probably fresh install)

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https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/1814124/+subscriptions

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