Chapter 4 (Return)
Page 68 This is the appearance of my beautiful wife. And he is described so interestingly here.
His eyes were warm and all-accepting but glinted with a hard scorn of anything that wasn't himself. His outfit, while possessing its own personality, did not show off any obvious features of characteristics. All in all, he was very difficult to grasp or classify.
I'll start with the first sentence. Actually, I am rather surprised that Narita described him in such a way as early as his first appearance. To me, Izaya reminds me of a mirror. He takes everything in, but does not produce anything of his own. Everything he shows is merely projected back onto whoever looks into him. It is written in a way that almost insinuates that there is, in fact, nothing belonging to himself to show anyways.

Onto the next part. Izaya being “difficult to grasp or classify.” Well, it's a funny way to describe such a strange individual, but it is very interesting to see that that is how others, specifically Mikado, perceive him. I have always believed Izaya is like an enigma; on the surface, he seems quite bland, like there is nothing of substance. Whether or not this is intentional and has something to do with the earlier sentence is only known to him. But once you look past that “blank” surface, there is so much inside him that it may very well just overwhelm you. I truly do think he is the most beautiful existence ever, and this only adds to that beauty.

Page 69
His congratulations were brief and clipped, but not devoid of emotion. He only used the barest minimum of emotion necessary in his voice, however.
This has me thinking: is Izaya Orihara the type of person who enjoys making new connections, but cannot maintain things such as bonds? For me, personally, I enjoy meeting new people and the like. But I despise the getting closer part. I would love nothing more than to keep everyone I know at an arms length, knowing only what I want them to know about me. Feeling people get closer to me is a terrible fear. I have to wonder… is Izaya like this as well?
He felt as though if he broke that contact, his entire existence would be denied, negated. Mikado didn't know why he felt this way—the man's gaze simply held him in place with its breathtaking sharpness.
It is interesting that Mikado has this feeling. To describe it as his existence would be “denied” or “negated” in the face of the man who claims to love humans so much… but even if Mikado were to look away, neither of these things would happen. Izaya would still love and accept his existence just as much as if he did keep staring back. His love is unequivocal, and balanced across every human.

Page 70
“It's not like a yakuza thing—he's just unstable. He's unpredictable. His motives and beliefs change every five seconds.”
Describing Izaya as unstable is good. It is fitting. Perfect, even. Izaya plays both sides, only going picking the side that comes out on top in the end. Is it because he just truly doesn't care enough to form his own personal opinion? Or is it because he does have his own opinion, but this opinion clashes with itself because it works in favor of both sides? Maybe he doesn't truly know what he wants.
Chapter 5 (Return)
Page 74
However, none of the people that Izaya had met had ever actually committed suicide. And that was very disappointing to him.
I have no real intricate analysis of this part, but I do want to note it down here just because it seems to be such a heavily misunderstood topic regarding Izaya.

What drove them to kill themselves? Did they have no other options? Were they prepared to die for the sake of others? How deep was the despair that surrounded them when they went?

Izaya Orihara loved people. Hence, he wanted to know them.

I think his insatiable desire to take in more knowledge is beautiful, really. Not so much the topic itself. I just find myself to be similar. I think it is beautiful to see him crave knowledge on people so deeply. In a way, it might be partially because of his own disconnect with the people around him. The second sentence of the earlier quote I think is directly linked to this. Its presentation makes it initially seem as if Izaya just simply wanted people to kill themselves. I don't really think this works, though. Because to love humans is to want to be able to observe them, no? And there is no observing the dead. I think the reason he is “disappointed” is because he does not get any closer to figuring out real, genuine motives for suicide. He is only getting empty, shallow reasons from people who barely even put any effort into it. I believe this to stem from his own desire for suicide, but he's much too cowardly to do it himself, so he wants to see someone go through with it first.

Page 75
“They think they're going to commit suicide and get to heaven! How impertinent.”
It is no hidden fact that Izaya is afraid of death. Terrified, even. And it is this fear that leads him to chase anything relating to the afterlife. I said earlier that Izaya is not the type to beg for mercy, or to let his desperation show, but I think that this pursuit of any kind of afterlife is desperate, even if he does not outwardly show it. He meets with all of these suicidal people, trying to figure out what they think the afterlife is… and when they give a different answer than what he thinks is proper, he is actually disappointed. Or rather, he is dissatisfied with their answer. He sees it as inconsiderate to death.
Izaya decided that these two were not taking the idea of death seriously.
This is similar to what I said up there. Izaya seems to revel in death, to fear it so much that he respects it. Or maybe respect isn't the proper word here. He holds it to a high regard, that is what it is. And so to him, hearing what he deems a middle schooler type response just feels like a mockery of death itself.
“Believing in a world after death is a right reserved for the living.”
I think… this is Izaya's way of saying that he believes if you are suicidal, you must be prepared to accept death, no matter what form it takes. You cannot be picky, essentially.

Page 76
“Izaya wore a smile as expressionless as a mask, and there was a coldness to it.”
Hearing Izaya's expression be likened to a 'mask' here is really interesting and also exciting. This is what I've always said! Izaya is like someone who goes around wearing various masks that suit all the people he talks to. But it likely backfired on him at some point, because now he's at a point where he can't tell the point where Izaya Orihara ends and the masks begin.

Page 77
"If you're dying to be released from suffering, does't that require a form of you afterward that recognizes you've been released from suffering?"
Although a good amount of what Izaya says here sounds more like a middle schooler type himself, I do think this is an interesting line. What good is “being released” from suffering if there is no you to appreciate it?
Really, Izaya speaks as if sometimes he is talking more inwardly, and sometimes it's just very flawed. It is almost as if he cannot fathom any other perceptions.

Page 78 He says something here that I said earlier.
“You shouldn't speak of the afterlife when you only half believe in it. That's slander to the afterlife. It's an insult to those people who were driven to death by the evil intent of others when they didn't really want to die.”
So he does hold death to a high standard, after all. To me, he sounds like an elitist. Haha, that's a bit of a joke. But really. He sounds like he takes death and the afterlife very seriously. So of course he would get unhappy when faced with people who seem to treat it so casually.

Page 79
“It's love. I don't feel any love in your deaths. And that's wrong. You must love death. You don't have enough respect for nothingness.”
There it is again. He worships death, virtually. His fear of it has led him to this state. I don't have anything else really to put here, but it goes with what I've previously said.

Page 81

Izaya ignored her jab, looking over the helmeted biker with great curiosity. Then, he asked, "Hey, courier. Do you believe in an afterlife?"

"What's this all about?"

"Just humor me. Consider it part of the contract."

"You'll find out when you die," Celty typed irratatedly into her PDA, then added, "How about you?

"I don't. So to be perfectly honest, I'm afraid of death. I want to live as long as I can."

Izaya is surprisingly honest about his fear of death. Personally, I'm a bit surprised to hear him admit it so openly. It is interesting to hear his thoughts in such a manner, though.

Izaya Orihara was an ordinary human being.

He did not wield extraordinary violence to evil ends and neither was he the kind of cold-minded killer who ended human life without compunction.

It was simply that he possessed both the greedy desire of a normal human being and the personal momentum to violate taboos if they stood in his way at the same time. He was not some charismatic mad villian, he just lived true to his interests. [...]

The kanji in his name were not typically read as "Izaya"—the name was a combination of Isaiah, the prophet in the Bible, and "one who approaches." He did not live a holy life fitting of the holy book, but on the other hand, he did exhibit an extraordinary capability to face new and different phenomena. [...]

He treasured his life as any normal person would, understood his limits, and spared no expense for his own safety.

This quote is a bit longer, sorry. I wanted to include all of this because it provides insight into just how Izaya lives. First, I think the fact that Narita starts this paragraph off by emphasizing that Izaya is human, and no more. I've always thought it was interesting that his parents named him after a biblical prohphet only for him to later develop something akin to a god complex. I don't want to say he thinks of himself as a god per se, because he is aware of his own humanity, but it's more of a sense of shame towards it. Maybe shame isn't the right word, but Izaya is someone who casts aside his own feelings and emotions, instead focusing outward on those around him. I believe he's said this before, and I will likely quote it when I get to it, but to him, getting involved will only make it more difficult to observe those around him. In this regard, he sees himself as something of an omnipotent figure, but does not look down upon humans.