Aha!
It seems like sometimes, for some reason, reinstalling the kernel packages 
renders grub-probe unable to detect the type of the filesystem for /, hence why 
it doesn't writ the btrfs-related bootflag...

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https://bugs.launchpad.net/bugs/752506

Title:
  new -8 kernel makes update-grub ignore writing subvol option for btrfs

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