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It's a possibility, but not a common occurrence by any stretch of the imagination: learning how to kill an unaware target quickly and discreetly with a blade is far different from learning to fight an armed opponent with a blade, and it takes a great deal of time to become skilled in either discipline. We have nothing to suggest that the members of the Skyrim Dark Brotherhood are skilled combatants save for perhaps two, and even considering that, the Penitus Oculatus are repeatedly described as elite fighters. And again, gameplay is not a good indicator of truth. Just because Penitus Oculatus armor seems to have a lower "armor rating" than Dark Brotherhood apparel does not mean that it is actually less protective, and one can clearly see how the effectiveness of different armor types changes between the games. Armor ratings are not based in realism, they are based on gameplay considerations.

Assassins aren't meant to fight directly, nor do they train for it. Sure, some assassins may also be skilled warriors, but this is not what an assassin is: it is not a given at all that a skilled assassin can hold his/her own in a melee. Other video games are hardly good sources, and historical evidence works against you in this: for the example you cited, not all "ninja" were specifically meant to be assassins. Others were trained to operate on the battlefield: it is an umbrella term, and not all ninja can be grouped into a single definition. What mainly differentiated "ninja" from other warriors, such as Samurai, was their lack of a code of honor, and willingness to do anything to achieve victory. Many were simply mercenaries hired by Lords because they did not care about exercising dishonorable tactics. And if you're going to be considering game-play, the only enchantments that Dark Brotherhood apparel possess are to aid in stealth and assassination: they do nothing to increase the durability of the clothing. Hardened leather is still protection, a form-fitting suit or a set of robes is not.

And who are we to say what the definition of "traditional morality" is when considering the Altmer, let alone considering the Thalmor? Morality is a social construct: one culture's sense of what is moral or immoral is not another's, and our sense of morality is going to be very different from that of a particular political demographic of another culture of another species in a fictional setting. To the Thalmor, the unmaking of Mundus is the ultimate moral act: the removal of mortality, the removal of distinctions that have caused nothing but strife, the removal of suffering, the ascendance of all to the same state of Godhood enjoyed by the Aedra, the Ge, and the Daedra. And mind that not all Elder Scrolls lore is solely present in the games: out-of-game sources comprise the vast bulk of it. The Dwemer became the "golden skin" of the Numidium, interpreted to mean that they collectively became the Oversoul of the Walk Brass. This was their ultimate goal: to become a God capable of destroying a universe that they had deemed false, to them a greater sin than anything. They did not want to live in the "false reality" of a Dream, and thus sought to destroy what they saw as a grand lie.

We're not treating it as bad writing because it's not bad writing. This isn't to say all of Skyrim is well-written, or that every facet of this quest in particular is well-written, but the Penitus Oculatus destroying the Sanctuary and killing the Brotherhood assassins within is not poorly-written, it is logically sound. Even if your analogy held, it would work against you: the Penitus Oculatus are well-established as elite troops, and demonstrate this in being able to destroy a Sanctuary of the Dark Brotherhood. It's not that Stormtroopers were incompetent "in reality", it's that it was an unintended effect of having them incapable of killing plot-important characters: lore-wise, Stormtroopers are elite forces superior to those of the Rebels, and demonstrate this "off-screen". Contrarily, the Penitus Oculatus very much demonstrate their competence "on-screen". And again, you're taking game-play to be far more accurate to lore than it actually is. "Levels" hold very little weight to them except to determine how easy or difficult it will be for the player to kill the character in question, and even so, as I said before: Skyrim's game-play mechanics are poor at reflecting different skills in different areas, and instead present an across-the-board increase in proficiency. Even within the skill categories, it's hardly a good indicator: skill with a dagger in assassination is incredibly different from skill with a dagger in melee combat. Skill with a bow in landing accurate shots at long distances, such as would be useful in assassination, is hardly skill with a bow in a hectic combat scenario. Assassins are not fighters: they are skilled at discreetly and quickly killing unaware targets and discreetly and quickly leaving the scene of the murder. They are not trained soldiers, and are not trained to fight in a close melee with other trained fighters: again, that any of the assassins survived at all is a concession, not a likelihood. That so many Penitus Oculatus agents died is a concession, not a likelihood.

They believe that reality as we currently know it has no value. As stated several times in this discussion, they don't want just to erase Man, but to erase Mer and Man at a conceptual level, to 'undo' them. That is about as Nihilistic as it gets. They aren't looking to erase mortality by removing death and decay from the situation. They don't want immortal mer and immortal humans coexisting. They are trying to erase mortality by erasing both Mer and Humans from reality. I'd argue that the Dwemer, on the other hand, were not necessarily Nihilistic, in that they simply were looking to remove themselves. If they successfully shifted to their own pocket dimension, then they arguably successfully ascended as a race. If they deliberately committed mass suicide, then yes, they were nihilistic to that degree, but they still didn't try to take reality down with them. Again, the Thalmor don't believe that existence has no value, and they do want to erase mortality: mortality is the curse that they are trying to undo. They believe that all suffering traceable to Creation, and that by forcing mortality upon the Ehlnofey, and thus forcing their degeneration into the mortal races of Men and Mer, Lorkhan committed an unforgivable sin. I've already shown that the definition of nihilism does not hold when considering the Thalmor: they are driven by a sense of morality, they hold to their long-established religious beliefs (and are, again, driven by them), and they do not wish to "destroy" any political or social institutions: they only wish to make them irrelevant. Arguably the Thalmor believe that political and social institutions are of great importance, as they are the tools that they use in the short-term to enforce order and facilitate their plans before the unmaking of Mundus renders them unnecessary. On the contrary, the Dwemer are precisely nihilistic. They did not only seek to remove themselves, they sought to remove everything. Their entire grand project, Numidium, was a means by which they would achieve Godhood and thus become capable of refusing the world: they sought to destroy Mundus, to destroy Oblivion, to destroy Aetherius, to destroy the Aurbis. It wasn't mass-suicide, it was transformation into a more capable platform through which they could act on their beliefs.

I still fail to see how it's bad writing: again, you're taking gameplay to be far more accurate lore-wise than it is. On armor: Again, the Penitus Oculatus agents are actually armored. Whether they are wearing cuir bouilli or whether they are wearing steel, it still gives them an advantage over assassins clothed in robes and thin form-fitting leather. On fighting skills: Again, assassination and melee combat are two entirely different disciplines. While some skills may carry over, a good assassin does not automatically make a good fighter, nor does a good fighter automatically make a good assassin. Skyrim's gameplay mechanics are poor at representing skill in particular areas, and instead represent an across-the-board proficiency in combat. Whereas the Penitus Oculatus are, like the Legion, well-trained in close combat, the Dark Brotherhood is not: it is not a guild of fighters, nor do any of its activities call for training members as skilled warriors. It only requires that members be skilled assassins, in order to carry out contracts. On the Penitus Oculatus' competence: They are not only the Personal Guard of the Emperor, they are the successors to the Blades and thus the inheritors of the Imperial Intelligence apparatus. It is repeatedly stated that they are an elite organization greatly superior to the Imperial Legion, who are in turn recognized as among the best warriors on the continent. Honestly, it's a miracle that any of the Brotherhood assassins survived. The assassins were outnumbered, inherently disadvantaged both in equipment and the nature of fighting, and quite obviously taken by surprise. Just because a sentry is posted does not mean that there will necessarily be prior warning, especially if the assaulting force is skilled and competent.

Not necessarily true. The Tong suffered from gross overconfidence in Shaie's assassination, branding it's own name on the walls with the Potentate's blood. It had risen to be a boisterous, public organization that was easily recognised and thus easily suppressed, and there is no indication that it operated in the shadows as the Brotherhood does. Its also worth noting that the unclear founding of the Brotherhood has raised questions about whether or not it WAS the Tong that assassinated Shaie in the first place. Fair enough point. Skilled assassins on home turf. Astrid, who is normally at the front door and should have been the first dead on realizing she'd betrayed more than just the Dragonborn had time to perform the sacrament. Nazir survived but Ambjorn goes down despite almost certainly having eaten far more hearts than any dragonborn werewolf. The Pentius agents are not particularly well armed, just having basic Imperial gear. Equipment matters more in gameplay than in does lore-wise, especially when considering skilled fighters in close-quarters rather than soldiers on an open battlefield. Even by that logic, the Dark Brotherhood is worse off: they have no armor, only a ridiculously thin (and impractical) robe or leather form-fitting suit. That said, you're also severely underestimating the quality of the average Penitus Oculatus agent: they are among the most elite of the Empire's troops, superior to the Legionnaires that are already recognized as some of the finest soldiers in Tamriel. It's important to remember that assassination is not combat, and one who is a very skilled assassin is hardly necessarily very good in a close melee. While the Oculatus would be better-suited for fighting, the Dark Brotherhood only ever emphasizes assassination: it's an assassins' guild, not a fighters' guild. That the Dark Brotherhood survived at all is a wonder, especially considering that they were outnumbered.

Handful of Penitus Oculatus troops: hardly easy even for skilled assassins, seeing as they're meant to be among the deadliest of Imperial agents. At any rate, it's important to note that assassinating an Emperor is generally considered a bad idea, and even the Morag Tong suffered harsh reprisals from all manner of Imperial Nobles seeking their destruction following their assassination of the Akaviri Potentate Versidue-Shaie.

They do not want to destroy it, they want to unmake it: there is a very big difference between the two. The Thalmor do not simply want everything gone: that is what the Dwemer and their Numidium want, and is counter to the Thalmor endgame. Rather, the Thalmor wish to unravel Creation, which they believe will undo the making of Mundus and return all mortal life to immortal et'Ada. Whether or not their plan would succeed, we do not know, but this is what they believe and what they work toward. Regardless of intent, undoing creation is pretty much the definition of nihilism. It may or may not result in a new improved (or old preferred) reality. On the contrary, it's far different from nihilism. Nihilism is, by definition, "The rejection of all religious and moral principles, often in the belief that life is meaningless." This does not apply to the Thalmor: they still possess morality (and arguably are driven by that sense of morality, as they see Mundus as nothing but a prison in which suffering is enforced by mortality), they still venerate their Gods, and they do not believe that life is meaningless. Rather, they believe that mortal life is a curse, and seek to return all living things to the state that they were in at the very beginning, which is to say the immortal et'Ada: they want to rid everyone of suffering by returning everyone to their previous state as Gods. The Dwemer, however, are nihilists. The Numidium most perfectly embodies this, and was specifically designed to "refuse the world" and thusly erase the Aurbis in its entirety.

Clans that are represented in-game are not all of the clans of Skyrim: if most were allied with the Stormcloaks, the Civil War would not begin tilted in the Empire's favor. The implication is that the people of Skyrim are roughly evenly divided on the issue: thus why it is a Civil War, and not an isolated insurgency or a revolution. Of the groups you listed, the Companions are neutral, seeing no honor in the squabbling of Jarls, the Blackbriars don't care who rules Skyrim as they retain influence and wealth either way, and the Thieves' Guild also doesn't care, seeing as they operate against the law no matter who determines it.

They do not want to destroy it, they want to unmake it: there is a very big difference between the two. The Thalmor do not simply want everything gone: that is what the Dwemer and their Numidium want, and is counter to the Thalmor endgame. Rather, the Thalmor wish to unravel Creation, which they believe will undo the making of Mundus and return all mortal life to immortal et'Ada. Whether or not their plan would succeed, we do not know, but this is what they believe and what they work toward.

Not disagreeing with you on that. Erasing the idea of Man is very different from destroying Mankind. That said, we really can't say for certain what would happen were the Thalmor to accomplish their goal of undoing Creation: it could very well be that they would simply be responsible for indiscriminate genocide, rather than a grand return to collective divinity.

You're severely overestimating the influence the Thalmor have in Imperial decisionmaking processes. Keep in mind that the Dominion does not have free reign to operate within the Empire, even to enforce the Concordat: the Justiciars are only permitted to operate in Skyrim, and even then were only allowed to do so due to the ongoing Civil War. There is a reason the Dominion organized the secession of Hammerfell and the Civil War in Skyrim: even in defeat the Empire is a powerful threat to Dominion goals,and the Thalmor do not control Emperor Mede or the Council. You're also misunderstanding Emperor Mede's character: he is a man who cares greatly for his people and the Imperial Dream, and was willing to risk his life in the Great War and then his public perception in the signing of the Concordat for the sake of the Empire's survival. While the Second Great War would not begin immediately, Mede would not stand idly as the Dominion killed, tortured, and kidnapped innocent citizens.

They're hardly evil: they are doing what they believe is good for all, not just for themselves. The Thalmor Leadership want ALL Ehlnofeic descendents restored to et'ada, Creation undone, and the very concept of mortality erased from the Aurbis. This necessitates removing Talos from the mythic and erasing the very idea of Man.

The Dawnguard are also not the Vigil of Stendarr. The Dawnguard were founded by one man, and it would be uncharacteristic of Isran to petition either the Empire or Ulfric for sanction.