"How are you so certain that your plans are flawless?"
Dumbledore's biggest problem is that he refuses to consider the possibility that he could be wrong about anything. Which is somewhat ironic considering that he is formatively traumatized by at least one time he was wrong, and it got his sister killed.
He seems to be focused on lamenting his past mistakes while denying that he could ever be wrong and insisting that he always knows best. Which is quite the brain twister, honestly.
And now Taylor's about to try and rebuild her reputation as Skitter. I hope she uses the DA and RoR to train herself and everyone else. A possible war-game exercise for everyone could feature the club trying to tag Skitter while she uses her swarm to capture and disarm them. Good combat experience for both sides, and it serves the bonus purpose of giving the wizards a heathy fear of the Queen of Escalation.
You're misreading Dumbledore. He is
used to being smarter and more educated than everyone else - and while he's wise enough to understand that just makes his mistakes larger, he's also old and set in his ways.
The man also has certain moral and temperamental convictions - which are not perfect, but at least very good for being a great teacher. And, because of long patience on his part, they have a tendency to work for the best in the long run - or at least he can persuade himself, based on his successes, that they do.
Dumbledore is also stuck in a position where - being a wizard - knowledge and patience and cleverness translate directly into personal power. This shoved him into the "big stick, mighty warrior, break glass when needed" box.
But. Because of his temperament & convictions, Dumbledore is a great teacher, a decent administrator, and a very poor general. Yet, people insist on treating him as all these things - and because of institutional inertia, it continues. (What, you don't think Dumbledore didn't have to be pressured to take the leadership the first time against Riddle?)
It doesn't help that, like many of the WWI generation, his formative experiences traumatized him away from ever developing a sound "morality of how to be a warrior". He's never needed or wanted either.
TLDR Dumbledore is a good schoolteacher and a powerful wizard, and because of that he's been pressured to take a bunch of positions he's not suited for. (Honestly, the man would be better served remaining Professor of Transfiguration rather than headmaster.) Institutional inertia and an overdeveloped sense of responsibility, as well as few other good options, keep him shackled to jobs he hates and is not suited to perform.
Dumbledore-haters are letting their trauma at authority figures not being perfect whip up a five-minute-hate towards a sad old man who's just doing his best to carry the world while yapping dogs bite at his ankles.
Still doesn't make the man a war leader, and he definitely needs to have some hard truths pointed out to him. Excellent, excellent characterization of him here.