Also, remember that on a failure (6-) you just get to make a GM move.  *ANY* GM move.  Time passes elsewhere and the evil ritual approaches completion.

Right -- Grim Portents from the GM's fronts can activate. Having all the hit points in the world doesn't help much when the big bad opens up the heckmouth.

What I'm saying is that all other variables being equal, puppy wrestling and troll wrestling have the same average results. So, the story is that puppies kick your ass as often as trolls. You can mitigate this somewhat with subjective success levels and throwing around custom moves. But even then, the story is, puppies kick your ass as often as trolls, unless we throw some excuses into the mix.

We've gone to great lengths to explain that this isn't so.

Side note, is there any way to account for task difficulty? For example, scaling a dangerous cliff vs. scaling a dangerous cliff in the middle of a blizzard without proper equipment. Do you just throw a modifier into the mix?

DW discourages adding situational difficulty modifiers to the basic Roll+Stat. If another PC is Aiding or Interfering, there's a +1 or -2, and a number of conditions or setup moves give a +1 forward (i.e. modifier to the next roll) or +1 ongoing (i.e. modifier lasting until a specified condition), but there's no task difficulty modifier in the RAW.

So instead of saying "this is super hard, take a -3", what the GM can do is say "you can't do it at all, unless you do X first" or "you start to do it, then thing Y happens that you have to deal with before you can finish it," or what Munin said, making the consequence for failure much nastier in the harder case. Maybe the GM says "there's no way you can climb this cliff face without any equipment" and someone else has to Spout Lore to think of a way to improvise some gear or Discern Realities to find an easier way up. Maybe the GM says "sure, roll Defy Danger with STR to start making your way up... okay, good, now, you get about halfway and then start to panic, roll Defy Danger with WIS to see if you can keep it together..."

It's worth noting that the six stat modifiers for a starting character will be +2, +1, +1, +0, +0, -1. The player will normally want to arrange to play to his strengths (e.g. INT +2 for a Wizard, who uses it on his Cast A Spell roll), but sometimes circumstances will require them to make a move with one of their worse stats.

As mentioned above, the 7-9 results are fairly clearly written out in the moves, but usually give the player some degree of choice in the outcome, as well. Sometimes the choices will be easy and sometimes they'll be hard, but at least the player gets some agency.

I need to be able to come up with NPCs that are unique and interesting

You can always delegate some of this to your players. "So, Vega and Lee, you guys are making the rounds of the hold, and Barker comes up to you. Vega, is Barker a man or a woman? Lee, Barker pissed you off a couple of days ago, how did he do that? Vega, do you care if Barker lives or dies? I mean, what is he to the holding? Is he useful? Who does Barker sleep with?"

When you don't know what matters, lean on the players to make stuff up. Share the workload. Bounce ideas off each other. At first the NPC factoids and connections will be random and not seem important, but do them anyway.

One one hand it doesn't matter if the PCs solve every problem by killing an NPC, because you're looking at NPCs through crosshairs - but if you've established a connection or a factoid about every NPC before you let them get killed, sooner or later the PCs will be facing someone who's connected to someone they've killed, and things start to get interesting.

It's unclear to me what the actual problem you have is. Give us some specifics.

Is the player actually micromanaging the hold? Does that make the player happy or unhappy? Does it make the other players happy or unhappy? If no one's unhappy, there's no actual problem.

The Hardholder has a lot of power, but a lot of problems at the same time. The holding defines a number of "wants", which define where the problems come from. Most of them aren't that intrigue-y, though the solutions to them might be partly political. If you've got an external threat in the form of "reprisals", "disease", or "famine", things might be too busy for the players to worry about the internal-conflict NPC, which is a great time for the internal-conflict NPC to make her move.

Messy and Forceful are interpreted by the GM; the object of the Smash! is named by the player.

As a GM, if someone dealt only 1-2HP of Messy/Forceful, I'd say they slashed the orc's face open, and blood sprays everywhere, and the orc falls back a pace -- but I wouldn't dismember the orc. With Smash!, it's not up to me; if the player hits 12+ and wants the orc to lose an arm, it's gone.

Messy/Forceful also won't usually take away the particularly important magic item your opponent is wearing. Smash! is ideal for getting Magneto's helmet off.

What do you want to do that you can't do with the rules as written?

"As you walk up the road Sweathog yells "take 'em!" and the guys on the rooftops to either side here start opening up with their Uzis. Fishstick, what do you do?"

"Crap! Is there anywhere I can take cover?"

"Yeah, there's a little kind of low shack where someone's been living, like a hobo in a box but made of sheets of corrugated steel, just beside you, but it looks pretty seriously rusted out. You can duck behind it, or there's a concrete jersey barrier up ahead that looks sturdier, you could try getting to that but you're going to get shot at."

"I run for the jersey barrier. Acting under fire?"

"Yeah"

"That's a 7."

"Okay, you take 2-harm but you're now under pretty solid cover. June?"

"I'm diving back behind the rusted-out shack."

"They spray some fire at it. You don't get hit directly but little rusty scraps are splintering off and spalling. Take 0-harm, but make the harm roll."

"5, I'm okay?"

"Yeah, a little rattled but you can act."

"I yell 'Sweathog, you've got two choices! You can put the guns down and we can talk, or, well, Fishstick brought the grenade launcher!' That's a manipulate, and I get... whoops, a 5."

"Sweathog yells back 'Grenade launcher! Great idea!' A second later, bam, it feels like you both got hit with god's own sledgehammer. The jersey barrier is cracked in half, Fishstick, you're no longer under cover, and you take 4-harm and you're stunned. June, you're going to have to act under fire to avoid getting pinned under the shack as it collapses..."