Yep, this is really messy..
Did 7 boot ups > restarts & got 4 different results

Twice got normal restarts that also included the pop up about 'remove media, 
press enter'
Twice got no pop up but the shutdown was text based & 'hung' on no particular 
errors, ctrl+c set it going again to a completed shutdown
Twice got the 'A start job is running for Hold'  hang
Once got the 'Wait for Network` hang (- only session where I enabled wifi..

The systemd timeout ones are the most egregious as they're no limit. 
Worst case scenario, is there any way to set all live session start/stop job's 
to a limited timeout? (30 sec or so max

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https://bugs.launchpad.net/bugs/1706939

Title:
  A live session can't be shut down due to "[ ***  ] (2 of 2) A start
  job is running for ... (21s / no limit)"

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