I finally got to confirm this. I had to install ntp to see the same
problem in my vm. Before that, openvpn was always running after a
reboot.

The moment I installed ntp and rebooted, I got the issue:
Mon Nov 20 19:17:41 2017 TCP/UDP: Socket bind failed on local address 
[AF_INET]10.0.6.10:1194: Cannot assign requested address
Mon Nov 20 19:17:41 2017 Exiting due to fatal error


root@04-57:~# systemctl status openvpn@server.service 
● openvpn@server.service - OpenVPN connection to server
   Loaded: loaded (/lib/systemd/system/openvpn@.service; disabled; vendor 
preset: enabled)
   Active: failed (Result: exit-code) since Mon 2017-11-20 19:17:41 UTC; 1min 
30s ago
     Docs: man:openvpn(8)
           https://community.openvpn.net/openvpn/wiki/Openvpn23ManPage
           https://community.openvpn.net/openvpn/wiki/HOWTO
  Process: 577 ExecStart=/usr/sbin/openvpn --daemon ovpn-%i --status 
/run/openvpn/%i.status 10 --cd /etc/openvpn --script-security 2 --config 
/etc/openvpn/%i.conf --writepid /run/openvpn/%i.pid (code=exited, sta
 Main PID: 612 (code=exited, status=1/FAILURE)

Nov 20 19:17:41 04-57 systemd[1]: Starting OpenVPN connection to server...
Nov 20 19:17:41 04-57 systemd[1]: Started OpenVPN connection to server.
Nov 20 19:17:41 04-57 systemd[1]: openvpn@server.service: Main process exited, 
code=exited, status=1/FAILURE
Nov 20 19:17:41 04-57 systemd[1]: openvpn@server.service: Unit entered failed 
state.
Nov 20 19:17:41 04-57 systemd[1]: openvpn@server.service: Failed with result 
'exit-code'.
lines 1-14/14 (END)

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https://bugs.launchpad.net/bugs/1689833

Title:
  OpenVPN server does not start properly on boot

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