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We have a solid few days at least. First there's the travel to Gridania and the night spent for Y'shtola to recuperate after being yanked out of the Lifestream. Then there's the time spent traveling to Dravanian Forelands > Hinterlands > Idyllshire. The time spent going to Matoya's, pilfering the Gubal Library, and then the subsequent extra nights for Cid to read, process, and make a concept real for the aetheric ram.
This really just spins back into the problem of the time bubble. We'll never know exactly how long it should've taken because the game doesn't have a concrete timeline for anything past the start of ARR.
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Tiamat doesn't exactly have her guard up, and like I said before, even if she can break out of the restraints there's no telling how easy it would be for her. She is despondent, and I'd say odds are equal that she'd just let them kill her, but even if she did resist, Thordan VII and his Heavens Ward would have the upper hand. Not too mention, when they beat Nidhogg, Haldrath has both of Nidhogg's eyes and keeps them at first. It's not until Nidhogg had Hraesvelgr's eye that he was able to start enacting his will on the ones with his eyes. Tiamat has no such knowledge, and would have no fall back dragon to seek an eye from. Dragons can sense one another, heck, eye users can sense dragons too. Hraesvelgr could sense Tiamat at Azys Lla, and he didn't even drop in to see her. In the days before we pierce the shield, there's also no avenue for Tiamat to leave. Basically, they didn't get them some nearly free eyes cause it wasn't in the script. That's it.
This still doesn't answer how Thordan would
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Well, even if that were so, it basically assumes that Mr. Pope-hat and Lahabreadloaf were operating under the assumption that we'd find a way to pierce Azys Lla's barrier. We did, but as I've said, it's days at the very least until we do that. The key from Bismarck gave them free reign of the entirety of Azys Lla. They could have still played the Ascians while getting what they sought.
Why would they not assume we'd come after them? We've never failed to find a way through all of the other impossible situations we've come across.