I did a couple of trusty→ xenial upgrades but could not reproduce this.

The first error in that log was this:

dpkg: considering deconfiguration of init-system-helpers, which would be broken 
by installation of upstart ...
dpkg: yes, will deconfigure init-system-helpers (broken by upstart)
Preparing to unpack .../upstart_1.13.2-0ubuntu18_amd64.deb ...
De-configuring init-system-helpers (1.14) ...
Unpacking upstart (1.13.2-0ubuntu18) over (1.12.1-0ubuntu4.2) ...

which got introduced by
http://launchpadlibrarian.net/222852012/upstart_1.13.2-0ubuntu16_1.13.2-0ubuntu17.diff.gz

This apparently leads to a dependency loop. The Replaces: must be kept,
but we could drop the Breaks: to make apt's job of  breaking such loops
simpler.

** Package changed: init-system-helpers (Ubuntu) => upstart (Ubuntu)

** Changed in: upstart (Ubuntu)
       Status: New => In Progress

** Changed in: upstart (Ubuntu)
     Assignee: (unassigned) => Martin Pitt (pitti)

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https://bugs.launchpad.net/bugs/1541914

Title:
  passwd depends on init-system-helpers (>= 1.18~); however: Version of
  init-system-helpers on system is 1.14

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