We are talking about a Sith Lord. Besides, he was a little preoccupied. And a bit of a jerk.
It's more a matter of internal consistency in your story than divergent game play. I wouldn't recommend anyone going out of your way to meet the criteria as it's currently implemented unless that's important to you. Thanks for checking it out regardless, it shows the checks are working, just not ideal for the quest flow since it encourages doing both quests in one go.
I've filed a bug, and hopefully there's a simple solution that will get it working without any player gymnastics.
Thanks all.