Note: this is a review for season 1 only, written prior to any viewing of season 2.
Given it's title, it's only natural to walk into Oreimo with the fear of it being shallow and perverted. Thankfully, it isn't, but I almost wonder if the creators themselves tried too hard to avoid that.
Oreimo's opening episode starts out the series with promise. We start by seeing that Kyousuke and his little sister Kirino, aren't in the best of sibling relationships. Kyousuke is annoyed at the way Kirino ignores him and is nasty to him. It's clear he wants to be on better terms with her. The door to that is opened too, when Kirino confesses her secret hobby to him: she's obsessed with Meruru and, in particular, the little sister eroge games from it. Oreimo handles this well, as such a thing could easily serve as the preface to a hentai scene. Instead, we see only some very subtle and slight sexual tension. Because we don't see Kirino's thoughts, and only brief bits of Kyousuke's, it's unclear if either is actually attracted to the other. This simply lurks underneath the bigger focus of the episode: Kirino's shame in her hobby, Kyousuke's acceptance of it, and the ensuing bond that comes from it. At the end, Kirino tells Kyousuke to play one of the games, and there's even a rather funny bit where he begins.
So it sounds promising right? Based on this pilot I fully expected Oreimo to tackle the brother-sister dynamic in an interesting way. It looked like Kyousuke was going to join into Kirino's hobby out of a desire to get closer to his sister, but that maybe some sexual tension would lead to huge problems.
But nope, nope, nope. Instead Kyousuke just kind of plays the game a few times without any consequence. He finds Kirino other otaku friends to help her out, and I'm honestly not sure what they contribute to the plot. Granted, they both work somewhat as characters, but for the most part they hardly even interact with Kirino and do little to nothing to develop her character.
Oreimo is one of many animes that also seems to believe in doing soft resets at the beginning of each episode. Conflicts introduced in one episode very rarely are addressed in later episodes, either because they have already been "solved" in a rushed fashion, or because the show apparently just forgot about them. This further compounds Oreimo's central weakness: IT DOESN'T MOVE ANYWHERE. Basically every episode is just a weekly example of how Kyousuke can help out his little sister. The only exception is a hodge-podge addition where he hangs out at a childhood friend's house, which is honestly worse as there is no clear reason why it's important to see. In the end the result is largely the stale story of a white knight male helping out a tsundere female, with the only notable distinguishing feature being that it's brother and sister.
The incestous aspect of this show could have made it interesting, but that wasn't the case. Occasionally the show attempts to use it for slight of hand tricks, but in such cases it's always executed poorly. For the most part, it's just a running joke that doesn't lead to any actual consequences for the characters, which leads into another point I'd like to make: Oreimo pretty much sucks at making good on the conflicts it teases. For example, in the very first episode Kyousuke finds the little sister eroge DVD and suddenly realizes, "This is the one thing I really shouldn't own!" and expresses fear for what would happen if his parents found out. Later, his dad finds out and doesn't give a shit, nor does anyone else who discovers this "hobby".
Furthermore, a frequent annoyance I had was how often the characters didn't behave honestly as human beings. Kyousuke's confrontation of his father was simply a bizarre interaction. Very often it felt that people simply behaved in dishonest ways to move the story how the creators wanted it to be moved.
The only thing more dishonest than the characters are the creators of this show. It sets viewers up with the expectation that it'll largely be about a brother-sister relationship, with the eroge/anime simply being a catalyst of sorts. Instead, it spends most of its time being an apologist for otaku culture. I don't hate otaku's or anything, but it's disappointing that Oreimo more or less just tries to shout at us to accept them. The point could've been brought across in a much better way. Furthermore, they spend way too much time on it. As a result the show basically ends up being about Kirino's hobby and Kyousuke finding ways to help her with it, which trust me, somehow manages to be even more bland than it sounds.
Perhaps I should move on to the positive things about this show. It is beautifully animated. The visual aspects of it look very good, there's some cool variation in what we see in it's OP, even. It's no masterpiece; there are many times when little sets it apart from a typical slice of life anime. But it's mostly very, very good.
Additionally, for all its flaws, Oreimo manages to be a mildly sweet story about how a brother comes to love his little sister (no, not that way). The final episode is well-done and does leave the viewer with some sense of feeling and closure. It's just that such feelings would have resonated much more strongly if their delivery mechanism hadn't been so predominantly generic.
Overall, I'd probably be lying if I said I'm not going to check out Season 2. Why? Because Oreimo does have potential. That much was clear to me. It just committed a slew of errors in execution that couldn't be ignored. I'm going to be optimistic and hope that things were better strung together in S2. I'll probably be wrong but that's fine I guess.