Regarding Ancalagon's deadliness, I think he should still rank above Glaurung. Ancalagon, though not as significant storywise, was still the greatest of the dragons and should be recognized as such. And even though he didn't cause as many main character deaths as Glaurung, there were no doubt plenty of deaths during the War of Wrath that can be attributed to Ancalagon.
Speaking of the War of Wrath, I believe that the winged dragons led by Ancalagon were enough to make even the Valar retreat, even after fighting through the rest of Morgoth's army (which probably included Balrogs). Were it not for Earendil, the battle could still have gone to Morgoth thanks to Ancalagon.
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