I try not to hold "charopers abuse this option because they've also convinced their DM's to let them take Iaijustu as a skill" against the design of the game.
I do, and a designer should, but that's neither here nor there. Nor is it the problem I have with the Factotum.
I had a Factotum (one of my aforementioned "not really useful in combat" characters) that was an absolute blast to play. That is the character that taught me the joys of Grease.
In or out of combat? That is the problem I have with the Factotum. Although, to be fair, it's not a problem of the Factotum design, but rather than the skill system still isn't to the place where it can support a skill based class.
as a strong seeker of narrative, fantasy, I want my classes to be specific archetypes that have a strong place in the world.
I think we have a lot of the same desires from a system, but we are plugging those desires into very different slots with different expectations of what a slot does. In general, I would never expect a class itself to give anything but the most vague descriptions of an individual's place in the world, and that mostly as a source of inspiration and not as a proscriptive 'rule'. In other words, discussion of the class might give you some ideas for the sort of background you might have, but it wouldn't tell you who you are. That would be up to you, the setting, and a discussion with your GM - who knows the setting better than the book's writer ever could.
So for example, a 1st level explorer (very generic jack of all trades martial class), might have backgrounds like the following that determine place in the world that the class simply cannot:
"I am the third son of a lower middle class family of teamsters. We make our living hauling cut stone from Stonechapel to Amalteen. It's an honest job, but not without its hazards, but are family prides itself as being as hard as the stone we haul and as strong as the oxen that pull it. My father has just died. He left to my oldest brother the family home, and the family business. To the next oldest brother, he left a team of oxen and the money for a bride price. To me, he left his sword. I don't get along well with my eldest brother. His hardness touches his heart, and has made him a cruel man with a cutting tongue. I don't want to work for my brother the rest of my life. I think my father meant me to seek my own fortune. I've bid my family farewell, and am looking in Amalteen for a small mercenary company or perhaps a small privateer that will allow me to sign on."
"I was a teenage runaway. My family were upper class furriers from a noble house of Ostland. But the open sea was my calling, and I wanted to sea warm and faraway lands. When I was 14, I ripped the sleeves off my shirt, and signed on as a cabin boy with a merchant. In the four years since that time I have been at sea and have seen many things, and am now accounted an able bodied seaman. A recent cruise was with Captain Terralse aboard a schooner called The Queen's Piranha. I soon came to realize that my Captain was not an honest man, but a conveyer of opium and other contraband and even slaves. One day, the Captain informed us that we would turn pirate, and waylay a small vessel. When I saw the cruel treatment that honest folk aboard the ship were subject to, and the Captain proposed to sell the passengers into slavery, I became upset and tried to aid the passengers in escaping. I was caught, and struck the captain in desperate fury. He beat me to a bloody pulp, and instead of selling me in to slavery, declared that munity should be punished by death, and decided to maroon me on a sandbar on a barrier reef that was only exposed at high tide. I am a strong swimmer, but in my condition, I could not possibly have swam the 20 miles to shore. I was sure I would drown or be fish food. Just when I thought I would die, I was rescued by a group of dolphins and a sea elf, who assisted me to shore. I've since made back some money, but I'm beginning to believe that I ought to do more with my life."
"I am a vagrant tinker, of Concheeri blood. I was raised by a prostitute and sold at 10 to a tinker to be his apprentice. Since that time I've been on the road. I can think of no better possible life than to be free of all obligations. Life is a grand adventure, and nothing delights me more than wandering into new lands. Over the last seven years, I've been up and down the whole Sword Coast, plying my trade as tinker, occasionally busking, or working as a farm hand when I can get no other work. But if I could find a way to make enough money not to work, I'd take it in a heartbeat."
"I am a Tumesi outcast. I grew up with the travelling people, but I'm cursed, and though my parents tried to protect me eventually my community threw me out. I'm fortunate they didn't drown me, as some wanted - to the old God Ugopoth, whose mark I bear. Now I must conceal my identity from people who hate me, and would kill me in even less pleasant ways if they new the truth. I tell everyone that I'm blind in one eye, and wear an eyepatch to conceal the wound I took from a tree branch. But often they suspect the truth, and make signs against the elder evils when I'm near. I was taken in by bandits, for my skill with a blade and other unsavory reasons. But when they saw what I really was, even they didn't want me near them. The eye underneath my eye patch works perfectly well but it is as bright pink, as the other is shining blue. Somedays, I think maybe I should poke it out myself."
And so on and so on. In 5e terms, we might have backgrounds or archetypes for 'explorer' if the ideas were strong enough and didn't overlap completely: sailor, pirate, tramp, tinkerer, lumberjack, planeswalker, guide, dungeon delver, archaeologist, etc. In 3e terms, we might support those ideas with feats, either customized to the idea or picked from more generic feats that supported the idea.
D&D is not "generic" fantasy. It is certainly broad and there's always been a strong emphasis in wide appeal (well, until 5e, at least so far), but it has always had its own identity.
If you go back far enough, you'll find that even if it has its own identity, it's not recognized as such. The people making D&D weren't setting out to create a non-generic system. They didn't expect every idea to be associated with every fantasy story, but they had a kitchen sink approach of throwing every idea from every fantasy story into the game, and they believed that if you wanted to emulate a specific fantasy story than you could do so with just a bit of tweaking and selection of the available options. In large part, I think this is still true, albeit we know 'better' now (and sometimes I think we are wrong) that the genera emulation was very imperfect.
I wouldn't use the term "setting" because that term, especially in D&D, comes with its own baggage (if you'll excuse the mixed lexicon). D&D is a very specific kind of fantasy; it is one where magic is split into two (or three, if you count Primal) different realms which not only have different sources but different practical applications (Wizards can't heal, Clerics cant magic missile, Druids cant summon skeletons). It is a game where Paladins serve a specific role and function (and 5e probably gives us the broadest possible range of options for the roles and archetypes performed by Paladins). Clerics get their magic from gods or their intermediaries; Wizards from study and use of their spellbooks. Magic has material, verbal and/or somatic components. Magic is broken into "levels". Fighters specialize in a specific weapon or weapon group or fighting style. Alignment. Races. Aberrations. Dragons.
All of that is true, and is what I call 'kitchen sink fantasy' and what I've heard called 'generic fantasy', since even if you don't necessarily find that in a lot of novels, most cRPGs end up looking like D&D with some small tweaks. And even in novels, there is more D&D out there than you think, and not just in Chronicles of the Dragonlance. Feist's works are D&D in every detail. So is 'The Deeds of Paksenarrion'. Bujold's Chalion setting very easily could be D&D, as could Sanderson's Elantris (which actually features D&D clerics). For that matter, 'Game of Thones' isn't that far off D&D in a very low magic setting with very few spellcasters, but at least some that resemble D&D clerics.
D&D both is generic and created its own generic genera.
So here's the thing folks: dissociated mechanics exist.
Yes.
any set of specific, arbitrary rules made to represent abstract ideas are going to have some dissociation.
No. Any set of rules are going to have some abstractions. Being abstract doesn't make them dissociated. While we are on the subject, being dissociated doesn't make them bad. In most cases, "class" and "hit points" are for example dissociated mechanics, unless you are playing Order of the Stick and breaking the 4th wall. The characters within the setting are unable to describe themselves in terms of their class or hit points, and are unable to make choices about them. They exist only in the metagame as abstractions of something real in the fiction. Characers in the fiction can make decisions about what they observe in the fiction - this guy is wounded, this guy has the profession and skills of a wizard - but they can't see "class" or "hit points". That in and of itself isn't bad. However, there are times when disassociation is bad.
Where there's room for debate is: how much that matters to any given individual.
I agree that some of this is personal preference. Particularly if the game doesn't spell out the connection between a mechanic and the fiction well, then something like spell slots of hit points can be a no sale for a player. And I'm sympathetic to that, albeit I think in this case there are good justifications for both and much stronger explanations for Vancian spell-casting in fiction than are usually advanced, and perhaps even stronger narrativist justifications for using Vancian spellcasting even when it is disassociated from the fiction's magical system. But, that being said, while some of this is personal preference and some of this is just what you are used to, there are cases when its very easy to predict when a disassociated mechanic is not a good idea, and that's when they are intimately tied to the player's proposition-fortune-resolution cycle or when they break the games normal proposition-fortune-resolution cycle or when they are going to regularly break with the fictional positioning of the game.
I'll give you an example I'm certain you haven't thought of that meets the third case - the price list in 1e AD&D. It's a disassociated mechanic that's given D&D more trouble over the years than hit points. The reason it is disassociated is that Gygax gives it a post hoc fictional justification, just as some many defenders of disassociated mechanics are prone to do when the disassociation is challenged. Gygax gives us price lists that are - as he well knows - purely gamist in nature. He knows that they are because we can tell from his other work that he's a good enough historian to know realistic prices. He then justifies his purely gamist prices with fictional positioning - the price list represents the prices of goods in a hyperinflationary scenario similar to the Klondike Goldrush. But why is this bad? Well, because it only tells us the mechanics for prices in a hyperinflationary scenario similar to the Klondike Goldrush, but as soon as the fictional positioning changes from that, we would expect that the prices would change. Gygax's post hoc rationalization leaves us ultimately with more questions than answers. Over the long run, players associated the mechanic by arguing that it was the list of normal prices - leading to published works calling out prices in the setting as being two or three times the prices in the Player's Handbook
because of the hyperinflation and scarcity of goods available. But this attempt at rectifying the rules ran into the trouble that elsewhere in the work, Gygax had used realistic prices (in silver pieces) for common labor, income from taxation, non-adventuring commodities, etc. The post hoc rationalization of the price list players were using in practice also didn't work. It wasn't until 3.5e put everything on a gold piece standard that the damage was undone and things sort of became coherent.
Most people would not care about this example, but the very fact that the changes were made over the course of the games history means that the problems came up and people did care. On the other hand, problem no one who didn't care was bothered by or even noticed the rectifying process of reassociating the price mechanics. Noone was hurt by 'fixing' it.
I'm hesitant to dig into this with more specific and more telling examples, because apparently there are some strong personal feelings around this. But I will dig a little more into this using Celebrim's patented 'World's Simplest RPG', to show that the problem with the world's simplest RPG is disassociation between the mechanics and the fiction. For those who've not encountered Celebrim's World's Simplest RPG before, it has only one rule - "Whenever the player proposes to do something, flip a coin. If it's heads, the player succeeds. If it's tails, the player fails." Technically, the entire RPG has about a page of rules, but the rest are so basic to RPGs that most people wouldn't recognize them as rules. The do things like define 'GM', 'Player', 'Game', and 'Story'. In terms of system, that's the sole mechanic of the game.
Celebrim's World's Simplest RPG is generic, universal, and coherent. You can use it to play any game you want. The elegant mechanic can handle every proposition the player possibly could have. They seem to work ok at first, if the player confines themselves to playing the game intuitively, and the DM develops post hoc justifications for why. In many cases, a coin flip is a good guess of whether something passes or fails. Hit it with your sword? Coin flip is fine. Dodge the sword? Coin flip is fine. Pick the lock. Again, coin flip. But the system will quickly fall apart. The problem is, regardless of who the fictional positioning says your character is, and regardless of what the proposition is, the system answers "Coin flip." And this creates disassociated mechanics. Or to put it another way, it becomes impossible to ignore that the resolution mechanics don't match the fiction. Superman tries to jump a puddle? Coin flip. Grandma tries to jump the Atlantic Ocean? Coin flip. More subtly, we don't yet have a rule for triviality. You want to stand up at your desk? Coin flip. You want to navigate to the bath room in your own home? Coin flip. This is a world that doesn't ever work like its stated to work, inhabited by characters who no matter what post hoc justification you give to the coin flip, won't be able to avoid noticing that their world is wacky land.
We can start talking about how we evolve the World's Simplest RPG in to 'The World's Minimally Playable RPG', and what we'd end up talking about is the process of associating the mechanics with the fictional positioning. How far we go along that path might be a matter of taste, but it's a real thing and it really matters in some areas more than others and not merely as a matter of taste.