One thing that’s stayed consistent about Obito throughout his entire time working under Madara is that he’s got a surprising capacity for ruthlessness. He’s willing to use as many people as he needs in order to achieve his goals – and here, his goal was to teach Naruto a bit of the reality he’s been exposed to as well. He could do a lot more physical damage than he did with the Juubi, but he wants to inflict a bit of despair onto Naruto first – he wants to cause pain. A lot of it. And destroying the alliance HQ just came with the added bonus of cutting off their strategic ability. To be honest, there’s a lot of truth in what he’s saying – Naruto will continue to see people die for him, thinking that he’s the key to victory, until there’s only him left. Although he really is the key to victory in this case. Even so, if he gives up, then they all die.
It’s a bit unsettling since we haven’t seen it for quite a while (also maybe because the entire cast was recently resurrected) but people actually die in this show. Kishimoto isn’t scared of killing off his characters from time to time, and Shikaku, Inoichi and Neji all got the axe this episode. Mostly Neji, though. It’s not really a big thing emotionally given that the Konoha 11 have drastically reduced in importance (and because it happened ages ago in the manga) but I think it’s pretty significant otherwise – Neji was one of the more prominent supporting characters, and he’s just died in a really anticlimactic manner. For all his optimism, Naruto looked oddly close to breaking there… and like with Pain, Hinata was there to lend a helping hand. She’s actually a better match for him than Sakura ever will be – Sasuke’s free to have Sakura if he wants. Neji’s death by Mokuton was actually strikingly similar to the situation in which Obito found Rin dead – he massacred all the Kiri shinobi there with Mokuton as well. One would almost think he decided to pick this on purpose.
Alongside all this, there was even more forward movement in terms of the plot – coming to think of it, this really was a great episode in comparison to the previous two. The Juubi is making its way through a series of transformations, and this is starting to reveal the cracks in the relationship between Obito and Madara. Even though they’re technically on the same side, there’s no love lost between them – Obito knows he’s being used, and Madara knows he knows. They’ll need a Jinchuuriki to control the next transformation, and with Madara sort of dead he’s not a viable candidate at all – meaning it has to be Obito who reigns in the Juubi. And even after that, Obito has to sacrifice himself in order to perform Rinne Tensei on Madara with his Rinnegan. While Obito thinks he holds all the cards, I’m willing to bet that Madara’s got something in his endless bag of tricks to subvert it all to his own ends. Maybe Obito knows that himself – so maybe we should be foreseeing a couple of betrayals and backstabbings in the very near future.