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: Kouta ascends to godhood by winning the Forbidden Fruit and takes away the Helheim infestation offworld; however, Earth is still recuperating from the invasion and there's much to fix after the Yggdrassil Corporation's secrets were leaked.
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.
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 Kouta suffers multiple breakings but has always managed to bounce back.On the other hand, his best friend, Micchy, was broken completely before the midway point and pulled a Face-Heel Turn.
Cool Shades: He wears a pair of sunglasses at every public appearance he makes. The photo on this page is actually an oddity for him, as even most pictures of the man have him with his shades on.
Cosmic Horror Story: A good number of his works are influenced by HP Lovecraft novels and the cosmic horror genre. He also names Stephen King, another dabbler in cosmic horror, as a major influence (particularly on Madoka Magica).
Darker and Edgier: If you're not sure how to darken the tone of your story, hire Gen Urobuchi. Under his purview, the darkness levels are practically guaranteed to get ratcheted up several notches. His friend Nasu jokes that he actually is a Reality Warper.
Fate Worse Than Death: Despite his infamy of being the "Urobutcher", killing off his characters isn't the worst he can do to his characters. He's also known to have his characters getting raped, being brutally tortured, or chronically turning the characters into monsters literally. In fact, he let some of his characters live, but have them go through emotional and mental suffering either seeing some of their loved ones killed off (Madoka Magica) or having their ideal dreams destroyed or exposed (Fate/Zero).
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 and Suisei no Gargantia. Kamen Rider Gaim deconstructs the concept as kids are the ones to get powers because the villains are exploiting their immaturity for all its worth, yet at the same time the kids often act more maturely and selflessly than the adults do.
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.
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-Passby 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 by either Sid (who's a Hate Sink) or Mitsuzane (who's become quite insane by the time he does so); and our hero Kota eventually more-or-less declares that his enemy is cynicism itself.
Unlikely Hero: Not only is he fond of this trope, but in an interview, he admitted that the people he view as true heroes are often these.
A hero is one that doesn’t want to be a hero. A hero is a one with all the possibility to make the choice but take the responsibility of the moment. And it’s really something hero has got to do. For example, in 9/11 some of the plane’s passengers fought with the terrorists. In Fukushima’s radiation leak, some people went and tried to fix the nuclear plant and died. But they have to do it. They are heroes. They don’t try to be heroes. They take responsibility and try to do what is right.
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.