YMMV / The Obsidian Trilogy

• Jerkass Woobie: Cilarnen for a good while. He's manipulated into moving against the City he loves, is found out, the fates of his friends and co-conspirators are kept from him and he's told his father is dead, he has his mage-gift 'removed' (muted and altered according to the villains' plans), which literally means he's given brain damage that leaves him suffering crippling headaches and without the ability that defines his life and identity, and then he's shoved out the gate into exile with an Outlaw Hunt soon following for good measure. He struggles a great deal for a long time in a world that's alien to him. Cilarnen is also much more heavily indoctrinated in City ways than Kellen was, and so regards the Elf who saves him and the Centaurs who take him in as subhuman and is horrified that they expect him to do chores. He was drilled in not making enemies and being polite to his 'inferiors' and is smart enough to recognize their kindness and charity, so he remains outwardly civil. Gradually his internal narration becomes less hostile and shows a grudging appreciation, and the Demon attack forces him to realize that he cares a lot about the people who took him in. Cilarnen never totally loses a sense of affronted superiority but he does become increasingly less of a Jerkass.
  • Once he's come around to being able to admit he cares about them he tries to express more genuine gratitude and repent for his uncharitable thoughts. The Centaurs, because he had the sense to remain polite and not call them 'talking animals' out loud, see him as a simple, Fish out of Water woobie and don't take his stiffness and obvious unhappiness among them personally.
  "Hyandur told us how they'd hurt you there - how they'd killed all your friends, and worked their evil spells on you, and chased you off with their horrible stone dogs, and still you wouldn't say a thing against them because they were kin. That would put anybody off!"
• Narm: There's a malign, poisonous influence associated with the Endarkened and their creatures which at the best of times is called "Demonic Taint". It's often instead called "Demon Taint" or just "Taint" and used in statements like 'It stinks of Taint' which especially in audio form is awkward considering the other meaning of 'taint'.
• They Wasted a Perfectly Good Plot: Vestakia's mother chose to have her child born entirely Demon in body and Human in spirit and personality. Vestakia's father has wings and a tail, strong magic powered by pain, and is immortal. It's also established that young demons have no need for sleep and all of them are mages. Other than being red-skinned with gold eyes, cute horns, and pointed ears Vestakia is totally human and has no magic but her sensitivity to Demons and Demon magic and an ability to communicate with cave spiders. She works with Healers during the war and could have discovered and struggled with an ability to use the pain of her patients; there is also the sequel trilogy set a thousand years later, and she isn't still around.
• Values Dissonance: Between this and Heralds of Valdemar, the series and main literary focus of the Obsidian Trilogy's coauthor Mercedes Lackey. In the Heralds setting it's generally agreed that messing with people's minds and making alterations without their knowledge or consent is perfectly fine if it's for their own good. Strawmen even appear sometimes to object and be shot down. Mostly this is done by essentially angels with an Omniscient Morality License, but not always. Meanwhile here in The Outstretched Shadow, the revelation that High Magic is powered by taking tiny, regular amounts of magic energy from the citizens of Armethalieh, who do not notice these donations, is treated as shocking and horrible, even though a portion of it is used in maintaining conveniences and prosperity for said citizens and healing them. The rest of it is used at the discretion of the High Mages who on the whole are not good people and maintain a restrictive stasis on the city, but Kellen is viscerally horrified and indignant about the whole concept, not just its misuse.
• The Woobie: Vestakia. Her mother and aunt were forced to leave their home and raise her in the middle of the howling wilderness. Then her mother died. Then her aunt died. And she started getting sick (literally) from all the Demons flying around. And non-demonic strangers usually attack her on sight. Plus the man she loves can't even tell her that he loves her as he risks his neck almost constantly. I'd say that qualifies.
  • Iron Woobie: On the other hand, she doesn't let any of that get her down. She makes a living herding goats all by herself in the wilderness. When she finds allies who don't attack her, she learns to use the illness-ability to help them track down Demonic influence, makes herself useful by becoming a Healer in the meantime, and is content to wait for Kellen's Mageprice to run its course before admitting her love to him. Vestakia just keeps on truckin'.