Indeed, thanks for the logs and your patience!

Mar 13 16:19:26 tigger systemd[1]: Stopped Network Manager.
Mar 13 16:19:28 tigger systemd[1]: Stopped target Remote File Systems.
Mar 13 16:19:28 tigger systemd[1]: Stopping Remote File Systems.
Mar 13 16:19:28 tigger systemd[1]: Unmounting /media/test_mount...
Mar 13 16:21:34 tigger systemd[1]: Stopped target Network is Online.
Mar 13 16:21:34 tigger systemd[1]: Stopping Network is Online.

So we need to fix that in NetworkManager's units, it needs to stop after
network-online.target and network.target.

** Package changed: systemd (Ubuntu) => network-manager (Ubuntu)

** Changed in: network-manager (Ubuntu)
       Status: Confirmed => Triaged

** Tags added: systemd-boot

** Summary changed:

- Manual cifs mount leads to delay on shutdown
+ Manual cifs mount leads to delay on shutdown - NetworkManager needs to stop 
after network{,-online}.target

** Summary changed:

- Manual cifs mount leads to delay on shutdown - NetworkManager needs to stop 
after network{,-online}.target
+ cifs mount hangs on shutdown - NetworkManager needs to stop after 
network{,-online}.target

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https://bugs.launchpad.net/bugs/1431774

Title:
  cifs mount hangs on shutdown - NetworkManager needs to stop after
  network{,-online}.target

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