Thanks, @nacc.
So, here's what I've done in the meantime:
- I've built another server with 14.04. Clean install, only OpenSSH server. 
Connected to an iscsi target. Reboot works.
- Upgraded the server to 16.04.02. Reboot still works. Guess my hunch was 
wrong. :(
- I've attached the journal as requested. You'll see that the iscsid daemon 
shuts down before the "logout-all.sh" script runs. Since iscsid has shut down, 
that script does not run successfully.

My machines that exhibit the problem use an iSCSI drive for:
- mythbackend (storage for recorded videos - that's the Ubuntu journal attached)
- postgres and mysql storage (Debian server)
- nginx storage (also on Debian)

Thanks for your help.

** Attachment added: "Requested journal file"
   
https://bugs.launchpad.net/ubuntu/+source/systemd/+bug/1569925/+attachment/4891508/+files/journal.txt

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https://bugs.launchpad.net/bugs/1569925

Title:
  Shutdown hang on 16.04 with iscsi targets

Status in systemd package in Ubuntu:
  Confirmed

Bug description:
  I have 4 servers running the latest 16.04 updates from the development
  branch (as of right now).

  Each server is connected to NetApp storage using iscsi software
  initiator.  There are a total of 56 volumes spread across two NetApp
  arrays.  Each volume has 4 paths available to it which are being
  managed by device mapper.

  While logged into the iscsi sessions all I have to do is reboot the
  server and I get a hang.

  I see a message that says:

    "Reached target Shutdown"

  followed by

    "systemd-shutdown[1]: Failed to finalize DM devices, ignoring"

  and then I see 8 lines that say:

    "connection1:0: ping timeout of 5 secs expired, recv timeout 5, last rx 
4311815***, last ping 43118164**, now 4311817***"
    "connection2:0: ping timeout of 5 secs expired, recv timeout 5, last rx 
4311815***, last ping 43118164**, now 4311817***"
    "connection3:0: ping timeout of 5 secs expired, recv timeout 5, last rx 
4311815***, last ping 43118164**, now 4311817***"
    "connection4:0: ping timeout of 5 secs expired, recv timeout 5, last rx 
4311815***, last ping 43118164**, now 4311817***"
    "connection5:0: ping timeout of 5 secs expired, recv timeout 5, last rx 
4311815***, last ping 43118164**, now 4311817***"
    "connection6:0: ping timeout of 5 secs expired, recv timeout 5, last rx 
4311815***, last ping 43118164**, now 4311817***"
    "connection7:0: ping timeout of 5 secs expired, recv timeout 5, last rx 
4311815***, last ping 43118164**, now 4311817***"
    "connection8:0: ping timeout of 5 secs expired, recv timeout 5, last rx 
4311815***, last ping 43118164**, now 4311817***"
    NOTE: the actual values of the *'s differ for each line above.

  This seems like a bug somewhere but I am unaware of any additional
  logging that I could turn on to pinpoint the problem.

  Note I also have similar setups that are not doing iscsi and they
  don't have this problem.

  Here is a screenshot of what I see on the shell when I try to reboot:

  (https://launchpadlibrarian.net/291303059/Screenshot.jpg)

  This is being tracked in NetApp bug tracker CQ number 860251.

  If I log out of all iscsi sessions before rebooting then I do not
  experience the hang:

  iscsiadm -m node -U all

  We are wondering if this could be some kind of shutdown ordering
  problem.  Like the network devices have already disappeared and then
  iscsi tries to perform some operation (hence the ping timeouts).

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