The fix for any Dungeon World GM conundrum is usually "Make moves!"

Here's the thing, in Monsterhearts you're playing people who have supernatural powers to harm and manipulate others. Prior to growing up, all of their powers are aimed in this way. The witch can hex you, the ghoul tries to eat you, the queen tries to rule you. You can can turn someone on, shut them down, force them to hold steady. You can spend a string to buy or force someone's cooperation.

But, when you want to talk sincerely with someone, express your love for someone, help someone unselfishly to become their true self, then you're on your own. You got nothing.

Nope. There's no helping in Monsterhearts.

I see my iphone corrected me into weirdness above. It should have read "the Ghoul who just LIED to Sylvia the Fae."

Right.  So, at worst, the druid gets one hold.  Can they then use that hold, shapeshift again, and instantly gain more holds?  

Could someone think of a situation "in the fiction" where this could not happen?

Druid: I use my pounce to knock down the Orc. 
GM: cool, so you land on top the Orc pinning him to the ground. You feel you body start to shift as the other Orc launches an arrow at you. What do you do?
Druid: I transform into a swallow!
GM: You could try but there's an arrow speeding towards you. Do you think you can maintain the transformation while being feathered?

To follow up on that; Operator mentions "your crew" in crew/contacts. Does the Operator get a crew automatically? How many people?

(Sorry if these questions seem obvious, it's just that reading through the playsets and rules seems to assume I already know the terminology like Juggle and such.)

They're good questions. Juggling isn't terminology. It just describes what the Operator is doing. Juggling a bunch of jobs, trying not to drop one.

Yes, the Operator gets a crew, made up of either PCs or NPCs. How many? How many makes sense?

Check the Gigs move in the Operator playbook.

Actually the Character Improvement chapter has "Gigs and moonlighting are in the operator’s playbook, page 70, in the character moves chapter, page 229, and in the crap chapter, page 262."

The game isn't about people who know who they are and what they want.

This only becomes a problem if the GM isn't making moves. Don't go around the table. Make moves.

While it sounds like an interesting setting, it doesn't scream Monsterhearts to me. With MH I'm more interested in why the Witch has the Vampire's hairbrush as a sympathetic token and what's going to happen to the Charlie, the Ghoul who just like to Sylvia the Fae.

I mean, in the scenario just described, if everybody HAD rolled well to defy danger (against being terrified), and then the wizard HAD rolled some good damage...the dragon would have died really fast.

You mean like the way Smaug died when Bard shot him with the Black Arrow?

[16 HP Dragon post]

Have you read the 16 HP Dragon post on Sage's blog?

1) What happened here recently? What should I be on the lookout for? What is useful or valuable to me?

Well, its obvious you interrupted some kind of shakedown. It's definitely the little urchin who stole your coin purse, but its not on him now. He's been roughed up pretty good too. Keeps blubbering "don't hit me!" If I were you, I'd be careful leaving the place. You're all alone here and anyone who's been in town half a day will know who you are and who you're traveling with. They may not like their odds if you get back to the rest of your friends. What's useful? Someone's left their hat behind. Must have fallen off in their hasty departure. Pretty distinctive too. Wide brimmed scarlet hat with a golden feather. Anyone who saw this hat and the person wearing it would remember.

2) Who's really in control here? What here is not what it appears to be? What should I be on the lookout for?

Well, its definitely not you. The lass obviously knows the land hereabouts. She could probably lose you in a second. It doesn't seem to be her either, though. Her eyes are sad as she beckons you onward. She is quite discomfited when you pause to adjust your pack. That's when you notice the change. One moment your looking into those furtive eyes and the next it's as if you're staring into two swirling vortexes that reach into your soul and threaten to unhinge your hold on reality. That's when you notice the knife....

Okay, I'll play.

1. A villager with a concealed item is being searched by Bulgur the Thief. The GM calls for a Discern Realities roll and Bulgur gets a 10. He gets to pick 3:
• What happened here recently?
• What is about to happen?
• What should I be on the lookout for?
• What here is useful or valuable to me?
• Who’s really in control here?
• What here is not what it appears to be?

Bulgur, which do you choose?

2. A beautiful woman beckons for Bulgur to follow her to his doom. Bulgur, not the trusting sort examines her closely. He rolls a 10+.

Bulgur, what do you choose?

1: If they don't care about it, it's not really leverage. It's something you thought was leverage.

2: Sure.