It appears my umount issue is caused by two things:

1) sshd no longer stops on lucid, due to an error in the upstart ssh.conf file
2) I did an upgrade of libc6, which caused the issue aswell

Atleast it looks like this is it for me :-)

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umountfs doesn't cleanly unmount / on reboot
https://bugs.launchpad.net/bugs/616287
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