House thinks he can escape the bombed out earth when he can't even escape the basement of the Lucky 38.
Because he's 200+ years old and stuck in his life support machine. Doesn't even matter when he can beam himself into a securitron as seen at the end of a House playthrough.
He acts like the wasteland is a lost cause when shit like the GECK exists.
True, but GECKs are few and far between. Even if the Legion and NCR weren't factors in fucking up the wasteland, you'd still have Khans (without a Bitter Springs gimping their numbers and spirit), the Brotherhood (without an NCR firefight to dwindle their numbers and corner them in a bunker), Fiends, Powder Gangers, other local raider gangs, the Black Mountain mutants, and so forth. There's a reason why he wanted three different malleable gangs at his disposal, in addition to his securitron fleet. It's only through sheer luck that someone like the Courier would be able to deal with all of those factors, in addition to the trouble in paradise with the three families.
He's supposed to be a super genius that could predict when the war was going to happen but he built his robot army and anti-nuke shield to need a day one patch, a patch he didn't think to build inside the area he could protect from nukes.
For one, the chip was to be delivered the day of the great war. The fact that the apocalypse happened the day he was supposed to get all his defenses operational was something nobody could account for. Two, you need to account for the time it would take to produce the chip in-house rather than in a factory that's already set up to manufacture it. When opportunity cost comes down to time, you'd probably go with the faster option - in other words, it wouldn't matter if he made it in his safe space or a factory, but he had no way of knowing that. The bombs were always going to fall on that exact day. His only mistake was that he wasn't more precise in predicting the apocalypse.
The only reason the chip wasn't destroyed in the war was luck.
So?
He failed to vet the Mojave Express to make sure it wasn't Oops! All Frumentarii. If Ulysses wasn't cripplingly autistic then House would've been checking his order status while Praetorians rig his bunker with C4.
That's why he had multiple couriers delivering different items. Only one of those items is of any actual importance, the rest were decoys. Yes, if Ulysses took that job, then he would have lucked into getting the item that actually has any usage had he bothered to deliver it to Caesar instead of doing his job normally. Additionally, the Legion was already scared to death of setting foot inside the bunker. Maybe they'd have been successful in neutralizing the security measures using machetes and throwing spears, but Caesar would be out of a lot more men than he's willing to send on a mission that is, at best, a curiosity to him. This is why he has the Courier go down instead. He's smart enough to know that whatever's down there can't be good for him, but is it worth thinning out the troops around your home base?
He had to rush to put together 3 families so the NCR wouldn't just steam roll him, 2/3 of said families have already betrayed him at the start of the game, and the third are cannibals.
You work with what you can get. He made a gamble on Benny not being a complete paranoid retard, and lost hard. If Benny wasn't so schizophrenic he might have been able to smooth things over with the Omertas the way the Courier could. A little naive to think the "former" cannibals wouldn't try to go back to cannibalism, even if they signed a contract promising they wouldn't.
Despite his treaty the NCR are chomping at the bit for the first opportunity they can get to kill him and steal his land.
There's nothing anyone could do to dissuade the government from taking what they want that you've got, outside of declaring war, which isn't the smartest thing to do when your (potential) business partner still has work to do throwing their men at the enemy. They're also highly incompetent and have no way of breaching his perimeter outside of the Courier, a choice that comes down to whatever you would rather do. Actually, in theory the NCR could raid House tower, but they'd want to use their best men to make sure they take down his guards. Best men that they're saving for the giant war on the horizon. Hell, they'd only want to kill him before the war is over because they have no idea what move he would make the moment they win or lose. Actually, no, given the showdown with Oliver at the end of the game, they had no idea at all that House was going to show up and demand the NCR vacate the region.
His star pupil he was grooming to be his right hand man hates him and took the first chance he got to betray him.
Benny is a wild card, just like the Courier. House's mistake was not realizing that Benny was a schizophrenic retard. He mistook a backstabber killing his previous boss to work for him as loyalty, rather than a red flag. That's on House.
His only life line is hoping a natural disaster in the form of a severely brain damaged mail man decides he wants to be a wagie.
The same could be said of the NCR and Legion. No matter what, the Courier is the deciding factor in winning the war.
He's an unbearable cunt that thinks there's only a big picture and that everyone else is going to see it the same as him.
That's true. A billionaire who's stuck in the past probably won't be able to convince anyone living in the radioactive middle ages that sending a rocket to the moon could possibly have any meaning to them.
Dumb fuck Wizard of Oz reference ass didn't even think to put a lock on the curtain he's hiding behind, then invited a completely unknown factor past all of his defenses, only to immediately start talking down to them, ignoring the yellow brick road littered with bodies behind them.
It is locked, it's just a lock that you're able to open. It's also a good assumption to make, that most people aren't petty enough to start killing and rampaging just because someone was snide to them the first time they met. Doesn't make much sense unless you're roleplaying as a psycho junkie. A bullet to the head is a much better call to kill someone than saying roughly "Your revenge mission can wait, I'm going to pay you a lot of money if you put it aside for two seconds to get the thing I want from your mark before you murk him."
It's one thing if you just don't give a shit about what he's offering Vegas in terms of "the big picture," but you can't deny that an army of soldierbots patrolling most of upper Vegas is a lot better than chaos in the streets like an independant victory, or incompetent NCR soldiers fucking with the locals and taking your money for inadequate protection, or the Legion wiping away any sense of freedom. He only takes taxes from the casinos, doesn't care about what you're doing as long as you're not massacring the locals, and is too busy focused on his stupid dreams of space exploration and rebuilding vegas to actually expand past his own territory. No conscription for you, no enslavement for you, no getting shot in the head while you're trying to enjoy a radscorpion casserole at the local diner with your family. He's literally too autistic to do anything needlessly harmful to his citizens.