Friday, June 23, 2023

This Is All Jeff's Fault

An Interview/Conversation with the first(?) OSR blogger:
Jeff Rients, of Jeff's Gameblog

 Q: So, you might be the very first OSR blogger, so one of the founders of the OSR? Am I wrong?

I might be the first OSR blogger. Maybe. I can’t recall anyone blogging about the sorts of things I wanted to talk about before me. But I could be wrong. The internet is a big place.

But I don’t really think of myself as a founder of anything. For one thing, there’s the very nature of the OSR movement as a look back, meanwhile there were plenty of people at places like the Knights & Knaves forums who never stopped playing the older versions of D&D. Who am I to those guys? Just some schmuck who finally wised up to what he had left behind.

Then there’s the people who really stuck their necks out by releasing the first OGL-compatible old school products. People like Chris Gonner with Basic Fantasy and Stuart and Matt with OSRIC. I think we’ve forgotten how brave that was. From WotC’s perspective, the point of the OGL was to support 3rd edition D&D, not create new competition. Even without a leg to stand on, the Wizards could’ve tried to sue those guys into oblivion.

Q: Why did you start Jeff's Gameblog? What was the public conversation about games like before that?

I had been pretty active at for many years and the quality of the discourse seemed to be slipping. The modding got quite bad and heavy handed, which is not uncommon on long-lasting fora, I suspect. But I couldn’t stand it anymore. At some point I decided I would rather shout into an empty blog-o-sphere than participate in that circus.

Q: You've run a LOT of games, con games, home games, store games, can you tell us about your experience?

I think I got the Moldvay Basic boxed set for my ninth birthday. I ran my first game a few weeks later. Jesus, that means I’ve been DMing for 4 decades now. 

My first con game as the DM was AD&D 1st edition at a small con in Central Illinois. I was so young my mom had to drive me to the con. Every player who signed up was older than me, some actual adults with grey hair and everything! One player, who I’m pretty sure was a college student, tried to run roughshod over me for the first half hour of the session. He wasn’t expecting a punk kid to be able to look him in the eye and say “no” definitely, but I had studied the gospel according to Gygax: the DM is the boss of the game.

As a teenager I did a little circuit of the tiny cons in central Illinois, sometimes as many as five cons in a year. I’d usually run AD&D and/or Call of Cthulhu. In college I ended up helping staff the con at the University of Illinois, called Winter War. I did that for quite a while after I graduated. In addition to staffing the con, I would run some D&D or any of a number of roleplaying games: Call of Cthulhu, Toon, Encounter Critical, many different versions of D&D, some HERO system stuff and probably lots of others I am forgetting. One time I even ran Philippe Tromeur’s Wuthering Heights Role-Play, which at the time was as indie as you could get. For many years Winter War had a multi-round AD&D tournament and I was in charge of writing it one year. That was my first experience trying to write an adventure so that other DMs could understand it.

My experience running store games mostly dates to the OSR period. A friend from the Winter War scene pulled off one of the all-time game nerd fantasies and opened his own game store. So I started with Labyrinth Lord there, but also ran straight-up D&D, Mutant Future, Boot Hill, Traveller, and an Encounter Critical mini-campaign set on Tatooine.

Q: What's your take on the Wuthering Heights game and how did it go when you ran it at the Con?

I thought it went pretty well. We spent the first 30 minutes or so building a relationship map (do indie games still use those?) so we knew who was related to whom and who was romantically entangled. We then played out a sequence of overwrought scenes where two or three people were put into conflict as a result of their relationships. One PC was murdered in a pique of jealous rage. That character got to come back in the climactic final scene as a vengeful apparition in a mirror who spooked his murderer, causing him to tumble down a grand staircase, snapping his neck in the process. 

Not a bad session for a game with no wizards or laser beams. However, it's an example of an early indie game that's almost all GM advice and mood setting rather than a tight set of rules. At least that's how I remember it. You could do most of what Wuthering Heights does with any old resolution system. Not that much would have changed had everyone been a 0-level character in a D&D type game or normal humans using FASERIP or a generic indie system like the Pool.

Q: So you got a Wuthering Heights game because everybody at the table wanted to play a Wuthering Heights game. After over a decade of accidental and largely unwilling research into the subject, I've determined that most of the folks in the indie scene think their favorite indie game is a genius game design because they only play them with other people who think their favorite indie game is a genius game design. Same goes for D&D, of course—its self-selection, we find our people.

It's weird to me that thousands of people who all know the same online friends, all play games written by these online friends, all write the same jokes, all hate the same politician-of-the-week and all write the same tweets about the shows that they all just watched the latest episode of still haven't figured out that the secret sauce of creative games is a shared sensibility.
You can always install a better sound system but a party is never better than its guest list.

It was advertised as Wuthering Heights in the con program, so I only got people who wanted to play Wuthering Heights, or at least wanted to play some indie hippie game, or were super open minded or curious.  That's actually a pretty broad range of possible players. Does that require a shared sensibility? An overlapping set of priorities, definitely, but if my play agenda is A and yours is B and, say, Jimbo's is C, then we just need to find the overlaps of those three circles to have a fun time. We don't have to all be on the exact same page. The only thing we really have to share is a willingness to play through the pieces that don't fit.

If we do a bit of B gaming or C gaming or B+C gaming, I'm perfectly okay with that as long as we circle round to A again at some point. Of course, it takes a fair amount of play to figure out what you actually want out of the hobby, so there needs to be a little wiggle room to test D as well, in case any of us like it.

Q: Well that part seems to go back to having social skills. People who have them not only can more easily move the game between A (which they like) and B (which is less their jam) but are also energized by the fact that other people at the table are enjoying B and so they have fun with it even if it's not their own specialty.

So maybe its not just shared sensibility plus—ok--its also knowing how to throw a party.

Yeah, that makes sense.

Q: I have this theory that a lot of the cliches of OSR GMing and taste preferences come from the fact that we're all just trying to get from "Hey who can play this week?" to "Yay we're actually rolling!" as quickly as possible—including relying on familiar rules and hacking mid-session rather than designing new games from the ground up. Do you think that's true?

You’re making sense to me, but I think the many distractions available to us in the internet era is another factor. When I was a kid, if we wanted to spend 6 hours making RoleMaster PCs, my friends and I didn’t have anything better to do, so that’s what we did. Nowadays if we go more than 10 or 15 minutes into a session without something interesting happening in play, I catch myself checking tumblr.

However, one of the hallmarks of the OSR was the willingness to go back and explore routes now disavowed or never taken by corporate ownership of D&D. We need to remain open to other possibilities, even if you and I seem to have settled on what we want out of role-playing. Or at least that's how it feels to me at the moment, that we've finally found the groove.

Q: There's a kind of advice you see outside RPGs which I think of as "Champagne advice" where you are trying to figure out how to do something and there's some Slate article that's like "How To Find A Home" and it's like "Step 1, Imagine your dream house" "Step 2, Travel the world looking at houses" "Step 3, Spend 3 months educating yourself on school districts" and it's like, yes, this is all good advice in theory, but it assumes the person has a lot of time and money that most of us don't.

I feel like, pre-OSR, there was a lot of early-internet advice about games that was not bad per se but it assumed we all had an infinite amount of time to make our games perfect.

So, like "How to make an NPC with depth? First, read all of Shakespeare..." etc. And the OSR was like "Just do a funny voice and the rest follows"--I feel like a lot of the resistance we got was along those lines. Like: Why don't you believe in 3-act structure? Why don't you see the importance of generating characters as a group in a separate session?  Like, this was the Champagne Advice. Am I talking crazy?

No, I don't think you're crazy. But I think it is a matter of priorities. Some people want to craft a character precisely. I'm happy with just some guy who can go on adventures. Some people want to hone a campaign world to precision, to get the kind of place you can plausibly set some fantasy novels in. You saw what happened when you made me answer my own 20 questions on the fly and I am quite satisfied with the results. We now have a backdrop for the party's shenanigans. That's all we really need.

If you go to a music store, you can buy a book on how to get started playing the guitar. It will walk you through the basics of getting started in an orderly, rational way. You can also take some lessons with an instructor. And if you stick to it, you're going to get technically better at playing the guitar. That's great.

I'd prefer to follow the advice from an old punk zine I have pasted into a journal. I'll scan it in and send it along to you, but the simple message is: here are how to do 3 chords, now go form a band. The obvious implication is that you can figure out the rest on the fly.

I don't think either path is better. Rather, what are you trying to accomplish? If you want to learn guitar for the joy of learning to play the guitar, the first path is right for you. If you want to do a show this Saturday where you and your friends shout nonsense into microphones, the second path is where you should be. Right now I am enjoying the heck out of the nonsense and the microphones. (Incidentally, I think this is connected to why I lean so much on crappy old adventures. Modern adventures tend to be too damn verbose and to presume too damn much. I'd much rather riff off a room that just says "3 orcs, 10gp" than deal with a page explaining who those orcs are and why they are there.)

And I don't assign this tendency to laziness, which I think it could be mistaken for. I am the guy who, knowing he was taking intro to Shakespeare in the fall of sophomore year, read all the plays and sonnets over the summer before.  I have turned in 35 page papers when the assignment was for 15-20 pages. I don't mind putting in the work. But the place I want to focus my limited attention and energy is the actual session, not prep.

Oh, and I forgot about some sci-fi I read a year or two back. Apropos of nothing, one day I decided I wanted to read every sequel that had been written to Edwin Abbott's Flatland.  The only ones I can really recommend to a general reader is A. K. Dewdney's The Planiverse and maybe Ian Stewarts Flatterland.

Also, Session Zero is of the devil. I didn't play a lot of different games in the 90's and 00's because of Session Zero. I'm pretty sure I almost played every single World of Darkness game from that era, but no session 1 came out of any of them. Ditto Amber and Everway. GURPS something a couple of times. And even an edition of Traveller where the ref insisted we do a joint chargen session zero. I've had campaigns of my own flame out after one get together, but at least something happened in that session!

Q: You obviously are capable of coming up with really creative content—your blog is full of it, but you mostly seem to take any crappy old dungeon and try to have fun making it sing. Can you talk about the difference between those kinds of creativity?

I seem to be capable of writing stuff other folks can use, but that’s what I might call preparatory fun. Though sometimes it isn’t even fun. There was a point during the writing of Broodmother Skyfortress where it felt about as fun as doing my taxes. The in-the-moment, painted-into-a-corner frisson of trying to make a crappy old dungeon work for me never seems to get old. If anything, I’m pushing myself further and further down that rabbit hole. For example: I didn’t even read the current dungeon you’re playing in before I decided that I was going to use it. I still haven't read several levels of it. I’m finding out some of what is in this dungeon mere moments before you are! And I am loving being up on that high wire, figuring out how to bend in the wind to keep the game going.

Q:  I don't notice you stumbling over the module too much. I tend to think an underappreciated aspect of being a great GM is just being able to keep the game moving fast, so nobody feels awkward—unless, of course, you're trying to create tension by looking up one of those "Oh wait did that fumble really kill you?" charts. I tend to tell new GMs speed is more important than almost anything, even more important than accuracy. Do you agree with that?

I don’t normally phrase it as an issue of speed, but I agree. I tend to think about in terms of the insidious desire to be a perfect DM. Better to make a wrong ruling than look up the rule. You can look up the rule and make an adjustment (or not) after the session. Players do this, too, of course. They can psyche themselves out trying win D&D, of all things. I’d rather do something stupid and get my PC killed than waste anyone’s time.

Q: Given how much fun you’re having just improvising off crappy module, do you see a role for elaborately thought-out traps or schemes or puzzles in what you do these days?

Sure, I just see them as ancillary to what I am trying to do as a DM. I have placed puzzles and plots and deathtraps in my adventures, I just never make them central to the adventure. If you don't go down the corridor with the thing I stole out of Grimtooth's Traps, I'm not going to relocate it. I try to never take the nonsense I have behind the screen as seriously as the players' actions in the game.

Q: You've got a masters in English Lit and everything. To me, that comes through in your writing and thinking about the game, but—and give yourself permission to be pretentious if you have to—how do you think that influences how you deal with RPG stuff?

How’s this for pretentious: 

Actually, I have a PhD now.

And frankly, that can make me a little bit jaded. I have no more patience for what passes for good writing in fantasy fiction. I can count on one hand the number of post-Tolkien fantasy authors I can stomach. I’m sure there are good modern voices I am missing, but I’m not going to sail a sea of dreck to find them. And RPG writing? How’s this for more pretension: there are no good RPG writers. At least not in terms of literary merit. Effective writers, yes. I respect the hell out of people who can effectively explain rules. And there are some snappy writers. S. John Ross writes both snappy and effective stuff. He’s my favorite RPG writer and I suspect he would laugh in your face if you suggested anything he wrote has literary merit.

Maybe this is one of the reasons I don’t care if I’m running a terrible old module from Judges Guild Journal: the field looks a lot flatter to me than to some people.  And some days I wonder if I read Lamentations of the Flame Princess adventures for the same reason that one guy from Hellraiser jams pins into his head.

These are not opinions I normally talk about because the last thing I want to do is bring someone down with my bullshit. But you asked, so I answered.

Q: S John Ross just reads like any old RPG blogger to me, plus he dogpiled onto the whole online hatemob thing, so I don’t really get it. I can’t think of any memorable sentences he’s written, and Encounter Critical just reads like pastiche—which isn’t easy, but if we’re talking PhD literary merit, Gygax wrote “Seldom is the name of Vecna spoken except in hushed voice, and never within hearing of strangers”. which is a lil awkward (“within hearing” scans suspiciously), but memorable.

Idolizing someone on this side of the veil is always risky business, I suppose. But I think you are wrong about Encounter Critical. It is full of memorable phrases and ridiculous ideas. I regularly reread EC for the sheer exuberance of the prose. Your point about Gygax is well taken. A little awkward but memorable describes a lot of his flavor text, I think.

Q: Your thesis was about how, in the 19th century, authors became aware of larger audiences for their work than the previously-presumed audience for literature, and this resulted in an expansion of  the role of “paratext”—that is, the explanatory stuff around the main text. I feel like there’s a lot here that relates to the RPG scene as well but—do you see that?

The growth of referee's advice, designer's notes and similar non-rules text can be seen as a similar response by game designers worried that people in the wild would play wrong. A major expression of this is AD&D first edition, which can be read as Gygax's attempt to reign in what he perceived as an "out of control" OD&D scene. 

And in some ways, he was right. The miniatures scene that OD&D grew out of used relatively light rules set and relied on referee fiat to resolve disputes. It was to some extent an oral culture where you learned how to referee from other players. The proliferation of OD&D introduced the game to a lot of people outside of that oral transmission loop. All the non-rule stuff in the DMG is for those people. AD&D1 isn't technically a paratext of OD&D, but the function is similar to how the use of paratext proliferated in the 19th century.

From this perspective, some indie designs start to look like more paratext than text, in that the mechanics are often shadowed by the part of the game trying to shape what users do with those mechanics.

Q: Ok: Tolkien. What’s your literature PhD take on him?

Part of me says not to take a swing at this question, since it is a bad idea to answer questions outside your expertise, especially when speaking outside an academic context. But here's my hot take: Tolkien is the one honest modernist, at least if you consider the rehabilitation of Western civilization as the great modernist project.

Q: I am now even more confused.  "In what way is Tolkien honest in a way (fellow modernists like) TS Eliot, Virginia Woolf, Le Corbusier and Jackson Pollock not?"

It is quite possible I am making no sense here. I must admit that I was wondering if "honest" was the right word for it. "Ambitious" might be better. I will try addressing the four people you name and see if I am more explicable to either of us.

Eliot - Prufrock comes to mind here, which I tend to read as the desire to go back and make everything right on a second try, to avoid all the normal human detritus that can accumulate over a lifetime. This looks to me like an atrophied attempt to return to the golden age, only the golden age is saying the right thing at parties. Maybe?

Woolf - I know almost nothing about Woolf. Did I read Ms. Dalloway in undergrad? Maybe. I've read A Room of One's Own, of course, where I'm pretty sure I first heard of Aphra Behn. (Incidentally, Behn's work Oroonoko would be good fodder for a LotFP adventure.) What is A Room's overall project? I'd argue it was women's liberation. But it is liberation still boxed in by rooms in big houses and piles of cash. Am I being unfair to Woolf for not being radical enough? Almost certainly. That's always easy to do I retrospect.

Le Corbusier - His plans for Paris? An attempt to recreate the Garden of Eden in concrete and parkways that fails to fully account for the fact that Eden was a space for two people, not twenty thousand. (Moshe Safdie's Habitat 67 seems to me like a step in the right direction in that regard.) Incidentally, once I took a diagram out of Le Corbusier's book The Modulor and turned it into a series of digital art pieces. The results were crude, but I expanded my photoshop skills in the process. So that's nice.

Pollock - Do I know jack shit about Pollack? I don't think so. I wrote a paper about one of his works once, but it was for a prof who was absolutely convinced that you could read Pollock representationally, i.e. that if a blob of paint on Pollock's canvas looked vaguely like Abraham Lincoln on the penny, then you could build a whole interpretation for the whole piece out of Lincoln, Civil War, slavery, etc. And that's what Pollock intended, according to this fellow. Pollock's works always looked more to me like an attempt to communicate a signifier without a sign. But I don't know that much about painting.

What I mean is Jolkien Rolkien Rolkien Tolkien's willingness to remake the whole world from scratch. I've not read any other modernist with the stones to burn the village in order to save it. Dude tried to rebrand God, right in front of the reader!

So what makes Tolkien more honest, or at least more ambitious?  He saw the flaws in the system just like everyone else, but he was the only one who was willing to wipe the slate clean and build it all over from scratch with new languages, a new heaven full of new powers, a holy kingship that is actually holy, etc., etc. It's the clearest, most humane statement of What If Everything Just Worked As Advertised, Please? that I have ever seen.

But it may be that I am in a cul-de-sac here. I've been slowly reading this absolute slobberknocker of a book on the origins of the Pentateuch, so I've been thinking about primeval stories and golden ages more than usual.

(Not to compare myself to a luminary, but I find myself recalling the Playboy interview of Kurt Vonnegut where he says something like, "You must remember that everything I say is horseshit." and the interview responds "Of course.")

Q: So who's a good writer to you, in fiction—fantasy or otherwise? (FYI I think M John Harrison is better than Tolkien.)

M John Harrison wrote a novel called Light, I think. It was mentioned in the designer's notes of a sci-fi spaceship wargame I was reading a few weeks back. I may have to check him out. Modern snooty 'literary' fiction I dig: Italo Calvino's If On a Winter's Night a Traveler..., Salman Rushdie's Satanic Verses and Midnight's Children (though it has been a long time since I read the latter), Ali Smith's Artful, Naguib Mahfouz's Midaq Alley, Kurt Vonnegut's Cat's Cradle and Julio Cortazar's Cronopios and Famas, which I read because you mentioned it on your blog. And of course the short stories of Borges. I suspect that Finnegans Wake is the best thing ever written in English(?) but I never could finish Ulysses. That says something about me, but I don't know what. I started House of Leaves but I had to put it down because I got the horrors. The only sci-fi novel I've read in recent memory is an old one from Norman Spinrad called Agent of Chaos, which I quite liked.  Have I read any fantasy lately? I re-read The Dying Earth a few years ago I guess.

If you want me to talk about pre-20th century fiction, I find Tristram Shandy and Thomas Carlyle's Sartor Resartus to be the funniest novels I've ever read (though Byron's poem Don Juan is at least as good if you can stomach long form poetry). I believe you are no fan of Bram Stoker's Dracula, but I love it. Mary Shelley's Frankenstein is probably the novel I've re-read the most times. I have trouble finishing the fantasy novels of William Morris because I get so emotional reading them that I start to cry. Until House of Leaves I would have picked James Hogg's The Private Memoirs and Confessions of a Justified Sinner to be the scariest novel I've ever read. I think LotFP referees would do well to read that last one.

But most of the time, I read non-fiction.

Q: (I now take a deep drag on the post-graduate salon's hookah pipe.) So (gesturing with two hands, dreamily) if I take seriously the notion that Tolkien's modernist radicalism was (roughly) the will to worldbuild this throughly, then could it be said that the postmodernist radicalism of RPGs is proposing anyone can remake the world, and make it work, too?

Oh, man. That's good. By my own ridiculous logic our need to imagine counterfactual realities ad nauseum is a postmodern aesthetic and political gesture. It's also maybe why some days I feel like I've fallen off the left end of the political spectrum. Not enough mainstream lefties I encounter are trying to imagine a weird new future. More importantly, it might explain why I was getting so annoyed at the boardgame Federation & Empire the other day. Are you at all familiar with the Star Fleet Battles corpus?

(BTW I used to smoke a hookah with an Egyptian linguist from time to time. She is cool as heck. Back home she had run a computer lab for women seeking education and employment until some local religious dipshits burned the place to the ground.)

Q: The only thing I know about Star Fleet Battles is what's on your blog. There's little ships and they move on hexes and each one has its own stats, etc.

Why were you so mad at Federation and Empire?

F&E is the strategic board game where you move whole Star Trek fleets around. The map annoys me because it uses fixed borders. The Federation is always in the center of the map, the Klingons are on the left and the Romulans on the right, etc. It takes the open-ended exploratory essence of Star Trek and nails it down as if it was an historical wargame. It's especially aggravating to me because a functional method for random placement of space empires with hidden movement was in print at least 4 years before it. Obviously, complaining that a game isn't the game you wanted is one of the lowest forms of criticism, but we could have had a Star Fleet strategic game where you start not knowing where the Gorn are. You dig what I am saying here? Or am I just being a grumpy nerd?

Q: Well it's not just that it leaves out the discovery element, it also makes it less tactically/strategically interesting because you're facing a known battlespace every time. So, yes, I know what you're saying.

Problem-solving against a problem that keeps changing seems like a thing RPGs and hobby games can be better at than most kinds of games.

So, we talked a bit about what you brought to the OSR, but I wanted to talk a little about what the OSR brought to you. You seem to read broadly in the OSR-o-sphere, what do you find yourself getting out of it? Has it changed over the years?

I don't read nearly as much OSR stuff as I used, but at one point I tried to follow the whole scene. At some point this became impossible. The rise of discord and similar venues is part of the problem here. I used to post in several RPG forums but lurk in many more. Now so much discussion is walled off from public scrutiny or even just a casual lurker. Two other critical shifts in the OSR are more about the infrastructure than the hobby itself: the rise of crowdsourcing and the golden period of Google Plus. 

Personally, things like Kickstarter have always looked too much like gambling to me, but I seem to be in the minority on that point, or else people have extra money they'd otherwise be throwing away at the casino. Either way, I can't deny that Kickstarter and Indiegogo got a lot of projects off the ground. Your Demon City and my Broodmother Skyfortress, just to name two minor cases. Whether I like the "give me a pile of money and maybe later a gamebook will appear in the mail" model or not, it has helped more people in the hobby get their ideas into other people's games.

G+, as a social media that organized gamers and games that was directly wired into a video teleconferencing tool, was a special era for the OSR. The distance between knowing a gamer and playing with them got a lot, lot smaller. My G+ campaign had 57 different players from all over the world. That was amazing! And I think it is worth noting that, since it was a Google product, it existed outside the scene in a way that things like Roll20 and DnDBeyond are not.

The biggest change to the scene in recent years is the appearance of the critical mass of 2nd generation OSR players. Many of these young people have little or no RPG experience outside the OSR scene. Can you imagine it? Being able to jump right into the good stuff without the D&D edition wars or the back-and-forth with the indie scene or talking about GNS theory? What a time to be a young gamer. BTW, I suspect that a lot of the cool RPG things I see published on are from this population.

Q: I was wondering, concretely, what have you picked up? House rules? Bits of grist to chew on? If you had to summarize what you were getting out of reading all this stuff (besides new players) what was or is it?

The biggest thing I have taken away is only to use complicated rules where the players like it. Spell descriptions, magic items, class abilities, that sort of thing. The rest of the time, the fewer rules, the better. That's why I use some of Raggi's simplifications. In particular, his flattening of AC and to-hits. FLAILSNAILS informs what kinds of PCs I allow in my campaign (no illusionists, otherwise I don't give a shit). And what rules I do refer to are much more mish-mosh than earlier. From '81 or whatever through 2000-something, if I was running a game, I worried about running that game correctly. Nowadays the basic infrastructure is '81 Basic/Expert D&D run very loosely, but I use Arduin crits, and the original OD&D 100xp/hit die rule, and 2e's wrestling chart, and the dropped lantern chart from RuneQuest, etc., etc. You remember the "magic" feather that helped Dumbo the Elephant fly? With regard to the rulebook, I feel like I've finally stopped holding onto the damn feather.

Q: Ok, there’s something to unpack here for veterans of game forum arguments. The best argument for care around rules is basically that it allows the player to know what tools they have to solve a problem.

Here’s a thing I notice you do: One of us wants to do some wacky thing. You go “Ok some chance on a d6” then the player goes “Ok, but wait, shouldn’t the fact I have a high strength (or extra arms, or I’m made of pies) make it easier?” and then you go “Ok, sure…” and propose a more detailed mechanic.

This works fine mostly because you’re experienced at improvising and because your players trust your sense of fairness—but do you think there’s some trick to cultivating that?

A lot of GMs seem to have a problem with less-detailed rules because they have trouble getting buy-in around that kind of casual resolution.

I think the whole issue here is a tendency to misunderstand the concept that the DM is the final arbiter at the table. That doesn't make you the sole arbiter of the good vis a vis the game. Old school play, at least how I envision it, works by consensus, by good faith exploration of a shared imaginative space. That space is malleable and negotiable right up until a resolution die is cast, so player input matters. I might be in charge of the game, but there are few "my way or the highway" moments under this model. I don't want the player to roll that die until it seems like they have a fair deal (though sometimes a "fair deal" is a 1% chance to avoid instadeath), which is why I tend to give a lot of time to opt out of a course of action before the roll.

And by the way, I want to hear the player say "But wait, my PC owns the Mighty Dishrag of Koza-Khan! That should give me a benefit on this roll!" It adds texture to the story and just seeing their eyes light up when they reveal an additional advantage is a delight. Nothing makes me happier as a DM than to see the players marshal their every resource to try to cheat death yet again.

Q: Totally! In Demon City I actually emphasize that when I can—combat's based on situational advantages in that game and so I say explicitly "This means players and GMs will be discussing whether a given thing gives an advantage—this is a good thing, because discussion supports the reality of the fiction in the game". 

Remember St Serpentor became a thing in your game?

Oh, shit. I am struggling to remember the details. That was in the Wessex campaign and you were playing Blixa the Thief. A giant tick scored some sort of terrible Arduinian critical on a PC named Gilgamesh (who I like to imagine as the real Gilgamesh doing some pandimensional slumming). And somehow there was a side conversation about Serpentor going on. The rest is murky. Gilgamesh survived a killing crit and somehow Serpentor got the credit. Please tell me you remember more than that.

Q: Well I remembered this detail from the attached (The classic GI JOE #50--the Battle of Springfield) —where Serpentor heated up a knife and pressed it to his wound, cauterizing it. So I was like "Hey can we try that?" and you said ok. And you gave us some dice chance to do it and we rolled and it worked and then we were like "All hail Saint Serpentor". And now you're stuck with Serpentor AND Gilgamesh in your setting.

Stuck with them? I'm not stuck with them. They're stuck with me!