I mean, he's really asking "how do I handle a 'what are the odds' skill check?" And the answer is, "let the fiction decide." AW is not particularly interested in making that one-in-a-million lucky guess. It's about setting up your fictional positioning so that it's NOT a one-in-a-million shot.

Cool! I learned fast that if you try to preplan any kind of story, the system will fight you tooth and nail. The characters and their moves are so powerful, and the players have access to the move sheets so you can't fudge anything or like, adjust difficulties or whatever. All you can do is let them have their way but make consequences for everything.

It's also sometimes good to straight up tell your players this. Like, "this game isn't really about fighting. It's about WHY you are fighting, or WHAT you're fighting for. Gunlugger, you are a badass, be a badass if you want. That rules! Your challenges won't be during combat, your challenges will be when combat is not an option."

My group rarely uses Read moves (which is a pity), but I could totally see that being an issue. It's all good, though, 'cause those moves are super fun no matter what. A hit? Awesome, they're lying to you, deal with it. A miss? Even better, things start going to shit. I love Read a Person.

If I'm having trouble thinking of a Miss, it's so easy to turn the question around and find out what the PC is really thinking and what their weak spot is. Handing out xp is totally worth it for that move because it generates so much good play at the table.

Aaaanyway, none of that has to do with your question. Here are some alternatives we messed around with:
1. Xp on all missed rolls, no highlights (mechanically stable but less fun than highlighting for behavioral prompts)
2. Xp on highlighted stats, but only once per stat, per scene (worked for us)
3. Xp by the book, with careful attention paid by all to the advancement rate (super metagame but whatevs)

That's some excellent presentation advice. If the character straight up has a move, like the Savvyhead is busting the safe, then she's entitled to know how long because the move says so. Otherwise, yeah, it's all "consequences and asking."

I kinda noticed that you referred to it as "your" story, too. That sounds like pre-planning but I'll give you the benefit of the doubt and assume that you feel like you're more invested than your players. So ask them what they're invested in. Be like, "hey Gunlugger, who do you trust around here? Who do you hang out with?" And do some scenes with them interacting with the NPCs they like, even if those NPCs are made up right then. Throw tons of townspeople at them and see who they react to best.

THEN, give those NPCs problems that can't be shot at.

If Battery has a problem with raiders killing his animals, then the Gunlugger can hunt down the raiders. But what if the animals are just sick? What if the "raiders" turn out to be starving kids in the woods? What if the raiders are one of the Gunlugger's OTHER friends? What if Battery's problem is that the Hardholder's taxes are too high? Can you really shoot your way through that?

Let the Gunlugger be a harass; that's why he chose the playbook. But also give him situations where being a harass just isn't the solution. He will probably love it, those are the best moments.

It is possible. I'm just saying for my MC money, as soon as someone says "we shoot them again" I'm going to back them down and ask "OK, So what is it you're trying to seize from them?" maybe the player says "their still beating hearts" in which case, fine. I still want them to stop and think about it for just a second because chances are if its not a battle, completely demolishing a gang was not their primary goal.

Absolutely. Needing four rolls to finish a battle seems like an edge case for sure.

I was a little curious, myself. Seize is often treated as the "combat roll," when it really encompasses much more. I think it can be hard to break out of that mindset, and realize that violence for its own sake is not really what the system is about. That said, it's totally possible to string together multiple goals and find yourself in the crummy position of rolling Seize four times in a row.