I've definitely had some unjunctioned fights with Gerogero because of that little "clever design choice".
The whole "work for the Owls until Timber is independent" thing doesn't really make much sense. Not only is it way too vague, but it's also sending out three new SeeDs for what could be a lifetime assignment. It really makes you wonder about Cid, because there's no way that adds up to a good decision to make unless he's already aware that Edea will be unveiled to the world *and* that she's gone into superevil mode *and* that events will arrange for him to send Squall after her. And I'm pretty sure he can't possibly know about the last one, and the first one is pretty implausible too. Second one is kind of an interesting question because I can't recall if there's ever a mention of when Edea got possessed or when Cid last spoke to her.
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We clasped our hands, our hands in praise of a conquerors right to tyranny