Hi,
thank you for your report, from the logs I see:

insserv: warning: script 'K36cups' missing LSB tags and overrides
insserv: warning: script 'cups' missing LSB tags and overrides
insserv: There is a loop between service plymouth and procps if started
insserv:  loop involving service procps at depth 2
insserv:  loop involving service udev at depth 1
insserv: Starting cups depends on plymouth and therefore on system facility 
`$all' which can not be true!
[...]
insserv: There is a loop between service cups and hwclock if started
insserv:  loop involving service hwclock at depth 1
insserv: Starting cups depends on plymouth and therefore on system facility 
`$all' which can not be true!
insserv: There is a loop at service cups if started
[...]
insserv: There is a loop between service plymouth and urandom if started
insserv:  loop involving service urandom at depth 4
insserv:  loop involving service mountdevsubfs at depth 2
insserv: Starting cups depends on plymouth and therefore on system facility 
`$all' which can not be true!
insserv: Starting cups depends on plymouth and therefore on system facility 
`$all' which can not be true!
insserv:  loop involving service checkroot at depth 4
[...]
insserv: exiting now without changing boot order!
update-rc.d: error: insserv rejected the script header


Mostly this is due to third party packages or scripts not palying nice with the 
packaged content form the archive.
You could start checking if all those files are actually from packages from the 
Ubuntu Archive - or if there are any external files involved.

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https://bugs.launchpad.net/bugs/1691880

Title:
  package openssh-server 1:7.2p2-4ubuntu2.2 failed to install/upgrade:
  subprocess installed post-installation script returned error exit
  status 1

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