Hi! c!Wilbur enjoyer/analyzer here! c!Wilbur had a lot of reasons for not pressing the button numerous times, some being that he just couldn't bring himself to, one being that he couldn't find it, and so on. However, the idea that he would actively kill other people (along with himself) if he were to press the button definitely played into it not getting pressed earlier!
To prove this point, I want to specifically bring up Wilbur's October 17th stream, which was his quick stream following the day of the Manberg Festival. This was also the first stream in which we, as the viewers, along with c!Tommy and c!Quackity, were shown the infamous Button Room. In this first Button Room scene, c!Wilbur explains that he intends to blow up Manberg after realizing that c!Schlatt was online and currently in Manberg. I also want to note that, apart from himself, Tommy and Quackity, nobody else was currently online or in Manberg except Schlatt. Wilbur would later go on to regard this as the best time to press the button and blow up Manberg.
βAnd I thought, what better time of just eradicating the nation and eradicating him than right now? I can finally do what I said I was gonna, you know, that I said I was gonna do.β - (Wilburβs Speedy Stream Festival What festival: 24:00, 17th Oct).
It is both implied and directly stated numerous times in this scene that Wilbur has no intention to kill/destroy anyone except Schlatt, Manberg, and, (something that feeds into the idea that he wanted to destroy himself far more than he wanted to destroy anything else) himself. This is a reoccurring message in this scene, actually! A neat quote to back up this idea comes when Wilbur is trying to justify to Tommy and Quackity why blowing up Manberg is a good idea. He says,
βWho else is it gonna hurt?! Itβs gonna hurt Schlatt, Manberg, and-β - (Wilburβs Speedy Stream Festival What festival: 26:55, 17th Oct).
Since Wilbur addresses later in this scene that he knows he is going to die in the button room, it can be inferred that the "and" was going to by followed up by himself. But regardless, this quote expresses one of the reoccurring themes of this scene: c!Wilbur does not believe, nor intend, that the button would hurt anyone else except for Schlatt and Manberg (and himself, but that kinda goes without saying so it'd be redundant for me to keep mentioning it in this post lol). In fact, he even uses this as a justification for him blowing up Manberg, that it wouldn't hurt any bystanders.
Now, the real big quote comes from when Wilbur is made aware that if he chooses to press the button whilst Tommy and Quackity are in the same room as him, he would not only kill himself, but Tommy and Quackity as well. Suddenly, a giant wrench is thrown into his plan, and he says,
βI donβt, I donβt, I donβt want to kill you two. I donβt want you two to die.β - (Wilburβs Speedy Stream Festival What festival: 28:53, 17th Oct).
c!Wilbur addresses that although he knows he'll be stuck in the button room, (He had said, "No, you two can escape. I'll be trapped in here..." earlier), he doesn't want to take Tommy and Quackity, two bystanders, down with him. And, in fact, this is precisely what stopped Wilbur from pressing the button in this scene, because Tommy was able to take this fact and use it in his attempt to convince Wilbur not to press the button yet. Tommy had already tried to use the "you'll die if you press the button" argument, but saw that it didn't work, as unfortunately with Wilbur's unhealthy mindset at the time, that was Wilbur's intention.
c!Tommy then takes the knowledge of Wilbur not wanting to kill bystanders like him and Quackity, and decides to block the exit of the button room, trapping himself and Quackity inside. Tommy presents Wilbur with a choice: Wilbur would be free to press the button if he so chooses, but if he does, Quackity and Tommy would die as well.
"If you press the button, we die as well. So if you wanna kill not only all of Manberg, but everyone...if you press it, then you kill everyone. Not just yourself."
And it works. Wilbur gets upset at first, asking why Tommy was "making this so difficult," and saying that he didn't want Quackity or Tommy to die, but eventually, when he was directly in front of the button, he decides to not press it. He decides to not blow everything up. He tries to cling onto Tommy and Quackity's plans and believe in them, instead. This scene is a great example of c!Wilbur choosing not to blow up Manberg or press the button due to the knowledge that he would be actively killing bystanders if he chose to do it.
You also mentioned October 16th, and the Manberg Festival! This is an interesting one, because it really does seem like c!Wilbur intends to blow up Manberg AND kill everyone inside of it, in this stream. However, (and I've also seen a bunch of analyists make posts about this as well, so they can probably explain this in more detail than I intend to in this response, since this is more of a side note than anything). I think it's important to note that whereas c!Wilbur did talk a lot of game about wanting to "kill everybody," prior to the festival, the actual events of the festival WILDLY change his motives and beliefs about this idea. Prior to the festival, c!Wilbur does talk about how he supposedly "doesn't care" if everyone else dies in this explosion. However, after the festival stream, this plan to "kill everyone" in the explosion is never really brought up again, and Wilbur never really expresses wanting to "kill" any bystanders in his explosion. In fact, literally the day after the festival stream, Wilbur has changed from "I don't care if anyone dies in this" to "I don't want anyone else to die in this."
There have been a lot of suspected reasons for this, but I think it comes down to Season 1 c!Wilbur being a very, well, naive character in a lot of respects. Even past the original L'manberg era. He tends to have an idea to do something, without really thinking about what it would entail, or what it would really be like to do something. He tends to talk a lot of big game in order to come across as a "strong, responsible, knowledgeable" person, like the persona he desperately wants to maintain for the sake of both those around him and for his own self-worth, when in reality, he is often just a regular scared guy that has no clue as to what action to do next, or what he's supposed to do. For example, when faced with the possibility that c!Dream could declare war on L'manberg back in the days of the revolution, c!Wilbur responded by saying that he could just say "no," ignore c!Dream, and refuse to go to war. It kinda goes without saying that this isn't really a realistic outcome for any situation of war.
In short, c!Wilbur thought he could just kill everyone during the Manberg Festival. He talked and talked about how he supposedly "didn't care" if anyone died in his explosion, but in the end, talk was really all it was. This is something that is actually proved during the festival itself! c!Wilbur, who had once tried to claim, and to convince himself, that he "didn't care" if anyone was killed, actively stops his search for the button and offers his own life in exchange for c!Niki's, and the rest of the crowd's. Wilbur, who had only minutes prior claimed he didn't care about Niki or the rest of the Manberg citizens, stood in front of Schlatt and said, knowing that there was a very good chance Schlatt would agree and he could die right there,
βJust, if youβre gonna kill anyone else, kill me. Donβt kill anyone else here.β - (Wilburβs The Festival: 1:10:53, 16th Oct).
c!Wilbur, as much as he wanted to convince himself that he didn't care about anyone else and was willing to kill them if it meant he could press the button, in the end, couldn't make himself not care about the deaths of others in his bomb plot, and ended up proving the point he himself wanted to be against numerous times! A lot of things could have prompted this switch from "I'm totally fine with killing everyone, yup, totally, mhm!" to "oh dear god wait i don't actually want this to kill anyone that isn't me, Manberg or Schlatt-" but personally, I think there's a very good chance that it was c!Tubbo's execution during the Manberg Festival. See, c!Wilbur could say he was fine with his friends dying as much as he wanted, but suddenly, one of his friends actually DOES die. Tubbo actually IS killed, and due to this jarring event, Wilbur kinda has to realize that he was, in a way, lying to both himself and others about his so-called motives, and that he didn't actually want anybody else to die.
So yeah, that's about it! :D
c!Wilbur talks a whole lot of big game, but he has indeed showed time and time again that he didn't truly intend for anyone else besides Schlatt, Manberg, and unfortunately himself, to be destroyed/killed in the explosion.
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