Got it! Sort of...

Misabling quotas make the system boot reliably.

No clue why. It may not be a race, rather the fact that the initial
quota check is supposed to happen only in certain cases.

No idea. Debugging boot with systemd is beyond my expertise.

Masking the systemd quota.service (the initial quota check) seems to be
sufficient to enable a reliable boot. Still I see failures on shutdown
related to the disabling of the stuff in fstab.

** Bug watch added: github.com/systemd/systemd/issues #4486
   https://github.com/systemd/systemd/issues/4486

** Also affects: systemd via
   https://github.com/systemd/systemd/issues/4486
   Importance: Unknown
       Status: Unknown

** Summary changed:

- Regression: yakkety does not boot (boots once every ~4 attempts)
+ Regression: quotas prevent yakkety from booting (boots once every ~4 attempts)

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https://bugs.launchpad.net/bugs/1635023

Title:
  Regression: quotas prevent yakkety from booting (boots once every ~4
  attempts)

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