I can't quite figure out why, but the answer seems to be "occasionally".
I was able to reboot a few times (2 out of maybe 30?) using the complete
list of reboot= options. However, I suspect making the reboot= changes
is a red herring -- I rebooted the machine more in the past few hours
than I have in the rest of the time I've owned it. It's entirely
possible that I would have gotten similarly lucky had I kept trying to
reboot over and over again without making the reboot= changes.

** Changed in: systemd (Ubuntu)
       Status: Incomplete => Confirmed

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https://bugs.launchpad.net/bugs/1619844

Title:
  [Xenial] shutdown/reboot hangs at "Reached target Shutdown"

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