sanitized is fine, I'm mostly interested in the dependencies. But they
look fine:

Before=umount.target remote-fs.target
After=-.mount system.slice network-online.target network.target 
remote-fs-pre.target systemd-journald.socket

i. e. it should shut this down before shutting down the network. But I
have a hunch that the networking goes down before that somehow, and thus
the umount hangs as it can't properly "sign off" from the server any
more. For that I would need the journal.

It's weird/sad that the debug shell doesn't work, but there's a plan B:
Enable persistant journal with "sudo mkdir /var/log/journal", then
reboot, do the mount, shut down, wait for the timeout, then reboot
again. Now do

  journalctl -b -1 > /tmp/journal.txt

and attach /tmp/journal.txt here. (the -b -1 means "logs from the
previous boot"). After that you are welcome to "sudo rm -r
/var/log/journal" again if you don't care about that.

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

Title:
  Manual cifs mount leads to delay on shutdown

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