Two of his 2013 works seem to deconstruct the former. The first is Puella Magi Madoka Magica The Movie: Rebellion, where Homura after a conversation with Madoka, realizes that Madoka may not be alright with her Heroic Sacrifice and that the only reason why she did it in the first place was because it was the right thing to do. So she takes matters into her own hands and rescues — well, kidnaps is a more appropriate word — Madoka and replaces her as the Goddess. Unfortunately, this action is bound to make the two enemies someday, thus hitting this back to a Bittersweet Ending. The next one, Kamen Rider Gaim seems to be complementing Rebellion, as in the middle of the story, Kouta wonders what he will do with his power and his advice is to "Destroy the law of nature that says hope is paid with sacrifice".
Break the Cutie: If there's an idealist in his story, chances are that person will be broken by the end. The Type-Moon wiki describes this tendency as the Reality Marble Dead End Catharsis: Heaven & Hell Drop, which lowers the luck of all characters in his stories by one rank.
Actually subverted in Psycho-Pass. Akane gets broken briefly after Yuki dies, but gets back to her idealistic self. In the end, Akane nearly gets broken, but learns to understand the cynical side of life while keeping her ideals and still mostly being an idealist.
Also subverted in Kamen Rider Gaim, as Kota suffers multiple breakings but has always managed to bounce back. His best friend Micchy, on the other hand, was broken completely before the midway point and made a Face Heel Turn.
Grey and Gray Morality: Also seems to be a fan of this, especially the kind that becomes obvious in hindsight, as shown in Suisei no Gargantia (the "aliens" are actually extremely modified transhumans, and both they and the still-human humans have legitimate reasons to hate each other).
Kid Hero: In an industry where most protagonists are under 18, he mostly avoids this, with the exception of Puella Magi Madoka Magica, Suisei no Gargantia, and Kamen Rider Gaim; the last of which is an active Deconstruction of the concept as kids only get powers because the villains are exploiting their immaturity for all its worth.
Actually averted in Psycho-Pass. Many people die throughout the series, but only a few main characters die; with only a one-shot character, one major hero and the main villain dying in the final three episodes which make up the climax and denouement of the work. Count those deaths and make note that this is Lighter and Softer for him.
Averted again for Suisei no Gargantia. Although a few characters die in the series (including fan-favorite Chamber), this series undeniably has the lowest bodycount yet. Maybe things are looking up for him after all...
Sliding Scale of Idealism vs. Cynicism: His works stand heavily on the cynical side of the scale, sometimes to the point of being nihilistic, but he says that he used to write works that still have a glimmer of hope in them. That being said, hisrecentworkshave demonstrated a gradual progression away from the cynical end of the scale; see immediately below for details.
Silly Rabbit, Idealism Is for Kids!/True Art Is Angsty: He is also definitely on the side of those who consider happy stories to be unrealistic, to the point where he has actually suggested that Lighter and Softer stories, by definition, contradict the laws of nature and are therefore difficult to write and impossible to believe.
"I have nothing but contempt for the deceitful thing men call 'happiness', and find myself with no choice but to push my characters, whom I pour my heart and soul out to create, into the abyss of tragedy."
Though Fate/Zero deconstructs heroism, the final conversation between Kiritsugu and Shirou shows that Kiritsugu at least saved Shirou, who would go onto try to be a hero like his father. Unlike Emiya who got nearly nothing for his struggles, Shirou does manage to make the world better in some routes of Fate/stay night. Emiya also does save the world by preventing Kirei or others from making a wish with the Holy Grail, which would bring destruction to the world, though Emiya does not get world peace like he wanted.
Gen Urobuchi seems to have some respect for idealism now, as Akane shows in the end of Psycho-Pass by keeping and believing in idealism throughout the whole series and then giving a speech on it to the Sibyl System.
And, finally, Gen appears to show full respect for idealism now, since the ending of Suisei no Gargantia had Ledo fully embrace the idealistic way of life on the Gargantia, and is also willing to make peace with the Whalesquid.
Kamen Rider Gaim continues this, as the most blatant anti-idealist speeches are given to the thoroughly unlikable Sid; and our hero Kota eventually more-or-less declares that his enemy is cynicism itself.
Kamen Rider fans had the same reaction when Kamen Rider Gaim was announced, though in this case he didn't deny it and even said that he took some of the darker previous Kamen Rider series as influences, while his associates joke about how kids will dislike drinking orange juice by the time the Wham Episode kicks in.