Well, it looks like the culprit could pretty well  be a wrong setting of
the grub-pc/install_devices_empty variable.

Checking each context I find :

Lucid (initial)             : grub-pc/install_devices_empty: true
Lucid (post reconf) : grub-pc/install_devices_empty: true

Whereas on a frech Precise install we have :
* grub-pc/install_devices: /dev/vda
   grub-pc/install_devices_empty: false

When upgrading from Lucid, the debconf values are wrong since even if
grub has been installed, the debconf values do not reflect this so the
first stage is not reinstalled, hence the failed boot.

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https://bugs.launchpad.net/bugs/1491894

Title:
  lucid to precise to trusty upgrade may leave system unbootable

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