My actual experience with the Operator is limited, but I don't see this as the trading, get-rich-quick Playbook. Like, at all. I actually have a lot to say about the Operator, in part because economics is a hobby and I know just enough to have opinions without actually being correct.

I see the Operator as the premier networker in Apocalypse World.  He's the guy who knows a guy.  In the broken-down market economy of AW that seems to be the default, he works more like a fence than a regular merchant.  If you just need leather chaps and seaweed crackers, you can just go into the marketplace with some jingle and buy them.  If you need something specialized, like forbidden tech/drugs/weapons/vices, or a special service, then the Operator's your friend.  Barter is just the currency that keeps things going, but especially if you've got an Operator in the game, you should probably work out some actual barter system that's appropriate for the setting with a cheet sheet that tells you roughly how many widgets things are worth, so that you can put some teeth into negotiations.  But I really don't think you should make barter the focus of the Operator's game.  He is all about the connections, the network of mutual obligations and benefits, keeping people happy and keeping his good name.  That's why his sex move is all about obligation, for the Operator everything is a gig and when he takes it on, he has to deliver.

His whole gig is keeping a network of reciprocation going across the fractured landscape and divergent cultures of AW.  Like it says in the playbook's flavor text, the Operator is guy who can look around him, find an insane doomsday cult on one side, and a paranoid dictator on the other, and figure out what each one needs that the other can provide.  The operator might not own a warehouse full of shit people want, but he's really good at figuring out who might want the shit which is in abundance in town X and how to make a profit arranging trade.  That abundance could be lots of rat meat, or a really skilled Brainer who needs work, or the service of a motorcycle gang to burn out some bandits in the hills that are messing up traffic. 

This seems like an impossible job, but you have to assume that the Operator is really, really good at what he does, maybe even supernaturally good, like how the Skinner can make a roomful of people stop shooting at each other just by taking off his/her sweater.  They are just awesome natural salemen and negotiators who can walk up to some paranoid bastard's fortified enclave with a business proposal and end up getting invited to lunch instead of getting shot right there on the driveway.  If you don't have that understanding of the Operator, I think the playbook won't work as well because the player will be afraid to put his guy in dicey situations. 

The Operator can be a good asset for the MC, I think, because, by their very nature, they have lots of reasons to go out and meet people and travel to interesting locations instead of holing up behind their walls like the Savvyhead or Hardholder.  The Operator also provides lots of hooks to other PC's, since it's one of the Playbooks that gives structure and makes it easy to define party relationships.  A Driver, Gunlugger and Operator would make an awesome trio for a road-based game, I think, though I haven't tried it.  You can also split the Operator against the other PC's by having him/her do business with the enemy or rivals of the PC's.  There's plenty of ways that the Operator's gigs can cut against the interests of other PC's or their NPC friends.  And heck, all it takes is one spoiled NPC boyfriend/girlfriend demanding discounts from the Operator on the stuff they want because  of their PC partner, and you've got a hassle for the characters to deal with.  Too easy. 

"What do you mean, you just sold Dremmer a rocket launcher?  He's a maniac!"

Finally, the Operator is one of the few characters who's got a strong interest in keeping the peace in Apocalypse World.  He/she doesn't want war, usually, because it's bad for business -- unless it's war to force open new markets. 

Fictional Operators that might be inspiring:
The Finn, from William Gibson's cyberpunk fiction
Yuri Orlov, the Nicholas Cage character from Lord of War (a good counterexample to what I was saying above about Operators being peace-loving)
Fagin: he's an Operator, and the kids are his crew, and you love him somehow even though he's a complete bastard. 
Henry Hill from Goodfellas.  Yes, he also pulled heists and did lots of other stuff, but all through the movie you see him schmoozing people, making deals, and above all, handling situations when things go wrong and business is about to suffer for it. If you're MC'ing a game with an Operator in it, watch Goodfellas again and take notes on how shit just goes haywire for the poor guy, mostly because of stuff his boss and crew do.
Mal from Firefly, well, yeah... sort of.  If we'd had the full five seasons, we'd have a lot more to point to with Mal doing business with people and taking care of things that go wrong.  As it is, we do seem him 
taking the Firefly all over the 'Verse to trade cargos and haggling with Badger and Niska, both of whom could be Operators in their own right.  This also illustrates how the Operator's gigs can help structure the relationship of the PC's and drive the story, even if the other PC's don't all work for the Operator the way they do in Firefly. 

tl;dr: Make the Operator all about mutually beneficial relationships and obligations, not just barter.  And keep the Operator's life interesting by making his business partners and crew demanding and occasionally unreliable, but don't make the world so hostile to him that he can't do business. In most holdings, there's going to be people who need him, and won't want to see him get shot.  He's more like to acquire new obligations in a sticky spot then get shot or tortured. 

Frank but friendly feedback is the way I roll, so here goes:
1)Wow, interesting concept but this is just way too on-the-nose for me to ever use in the game. 
2) There's an awfully big straddle between the literal and figurative meanings of "eating shit" and I don't think it quite works. 
3) The whole playbook seems to be more about masochism than about eating disorders to me, although I'm only a mild expert in either subject (I work in mental health).  In my (limited) experience, eating disorders tend to run hand in hand with serious control issues. The kid who tries very hard to be perfect but has this urge that builds up over time that they can't control seems to fits Monsterhearts better than the one who wallows in their dysfunction.
4)Getting power through humiliation is a cool idea, I'd like to see other Moves that that cover the whole range of what might be interesting and useful in a Monsterhearts game, particularly things that could be done in semi-public, like while having a private conversation at a table in the lunchroom or while walking around the neighborhood.

In my Gaga game, there were a Savvyhead and a Brainer, and one of the things I did during the first session was have the NPC Hardholder ask the Savvyhead how those anti-Brainer devices were coming along.  This created full-blown paranoia in the Brainer's player, not just the character, and worked wonderfully well at splitting them up and creating PvP tension.  In general, the Brainer seems to be pretty easy to split away from other PC's.  If I were playing one, I'd seek to become best buddies with someone like the Gunlugger or Quarantine early on.

The Brainer's greatest vulnerability, I think, is that the whole Brainer gig is something of a paper tiger; yes, you can screw with people no end, interrogate their brains and implant commands, but if you go too far, you'll discover that four guys with guns and shivs are more than a match. This is such a classic situation, it even made it into the rulebook as the example of combat.  I wonder if the pain wave grenade was created for just such a situation, it's the Brainer's best defense against being dogpiled by angry citizens. 

Hi, getting back into gaming after exams and I've been on a Civil War kick (American Civil War, the blue and the gray, brother vs brother etc), and it struck me that it was pretty darn apocalyptic and you could totally set an AW game in someplace that saw heavy guerilla action like Bleeding Kansas or Tenessee or Kentucky, or, if you want more of a deep South flavor to your chaos, Georgia during Sherman's march.  I've been thinking about pumping up the chaos with something like "Vicksburg flu" wiping out half the population or zombies or a just a nightmarish War Between the States that keeps going and going, with more and more destructive weapons and tactics, until the civilians are equally terrified of both sides' armies and things have gotten weird and steampunk.  But I'm not sure any of that is necessary, since it was disastrous enough in the historical version. 

Any way you situate it, there's a setting of chaos, violence, scarcity, and crumbling authority, raging ideology and people shooting each other for minor reasons or no reason at all.  If the game goes well, there might be a sequel in the weird west.  For most of the playbooks, I think I can get along without huge changes, maybe adding a little steampunk or Southern Gothic flavor to the settings depending which playbooks people use and how they use them. The Brainer and Savvyhead might be a little tricky since they're both using the lost technology of the ancients, but maybe the Brainer could be reskinned as a Mesmerist or just a creepy occultist.  The Chopper and his gang are mirrored pretty well by a guy leading a rogue cavalry unit or something like Quantrill's raiders, outlaws on good horses with guns.  The Driver maybe becomes a horseman or scout, with more emphasis on freedom and riding the range and less on cool cars.  Also, he doesn't get "My Other Horse is a Tank."  I'd love to reskin one of the playbooks for the railroad, but it feels like something that needs its own playbook, or maybe a specialized Savvyhead or Operator.  Among the LE playbooks, the Faceless and Maestro D' fit perfectly, the Solace and Touchstone could be tied in to liberation and the Underground Railroad beautifully.  The Quarantine, probably not unless you want to imagine some Revolutionary War hero who got put into suspended animation by Benjamin Franklin to sleep until the Republic faced its greatest crisis.  That might be a little weird. 

Finally, for Civil War AW, along with the usual character creation options, you also have to choose one more:
Facial Hair: Clean shaven, enormous sideburns, enormous mustache, enormous flowing beard and mustache, pointy chin-beard, pointy mustache and chin-beard, [your favorite general or politician here]
These days, some of the players may be able to say that their character has the same beard they do with perfect historical accuracy. 

I'm totally stealing the Burial Grounds for my Monsterhearts game set in Seattle.  That's awesome. 

Did you have the whole episode planned out, or were you running it Sorcerer-style, just throwing out Bangs at the players and seeing what happens?

Yeah, separate lines happen in every game I've been in, in part because there's no reason to be a "party" and every character has their own job to do.  I like to think of AW characters in subgroups and find reasons for odd pairings when it comes time to frame a scene -- maybe the Chopper is escorting the Angel to a crash site where one of his guys is too badly hurt to move, for example. 

I find that people don't mind as long as you switch back and forth fairly often -- every time things get really exciting or suspenseful is good, like when the Chopper runs into an ambush or the Angel finds someone waiting for her in the infirmary.  It keeps the player excited to get back to the scene, and they have time to think about what they'll do. 

I also find it helps to have an expectation that other players can participate in the scene, if only by comments or encouragement.  And it's good to check in with the players and see if you can jump ahead -- it's a lot easier to combine paralell story lines if they're not too long and involved.

I have AW in the queue to run after my current Monsterhearts game, I'll see if anyone wants to play the Abacus and see how it works in practice.