Wait, what? Suckering someone is a thing, but it's separate from Go Aggro,

And I have a bad memory.

1. Sure! They can refresh the hold, it's just another opportunity for that hold to go the other way.

Plus potentially having to seduce/manipulate or (whatever Go Aggro is called now) the NPC every time you want to arrange time and solitude. Sure the PC probably has Hot+3 but if it matters to the NPC to get out from under all that hold, he's not going to let the PC refresh it without having to succeed in two rolls every time. Sounds like that NPC is now a Threat waiting for a low roll to crop up. Or maybe his friends are the threat.
"Rolfball is willing go with you but Dibbs, the guy who runs the motor pool (which the Savvyhead, Driver and/or Hardholder have a stake in) where Rolf works steps between you and the door. 'He's got work to do. He's not going anywhere', he says, thumping a lug wrench in his open palm. What do you do?"

Still being a fan of the character, definitely making AW seem real. Just playing NPCs simple motivations off of each other and potentially creating a PC-NPC-PC triangle. The PC has a lot of dramatic options at this point but they may not be good options.

It depends a lot on the PC's. For example, if the crew includes  the Hardholder, the Maestro 'D, the Hocus and The News, they're pretty much going to determine what the average person is. The average person is part of the civilian population of the hold, who does whatever it is the hold options say he does. Some of them will be patrons of the establishment or members of the Hocus's followers and most of them listen to the radio. If the hold has a bustling market, some of them are out of town traders. Basically, anyone who can be considered "average" has a minor role in the society of the game.

In an even more general sense, my impression is that the wealthiest, most impressive hold has a quality of life roughly the same as the Old West. Most people are going to be finding food (by scavenging or growing), finding something they can sell to traders (like mining or scavenging) or offering a service to the people who do those things and their primary concern in life is to keep living. The average person doesn't have too much trouble covering their 1-barter a month as long as they're willing to put in the time. They won't think much of saving up or changing the world. Doctors are rare, so everyone knows a little first aid or folk remedies. Violence is sadly common, so everyone is armed, even if it's just a rusty old kitchen knife they've sharpened. On the whole, though, a sense of a larger community holds together. There are only a couple of fundamental scarcities and when people don't get them, the Hardholder and company have to find a way to cover the gaps. (Side note, now I want to play a Battlebabe Shreiff!)

In a poorer area, where the average person struggles to find 1-barter a month, it's more like a game of This War Of Mine. People break up chairs in ruined buildings for firewood to survive the night or kill each other over an MRE. Everyone is still armed and they're a lot more likely to fight to the death if the alternative is losing one of their key survival tools. Any kindness is a huge surprise to them, to be taken advantage of mercilessly or to be repaid by someone dead shocked that not all humans suck. The biggest social unit is more "pack" than "society". The fundamental scarcities are basic survival needs. When they're not met, people get sick and/or die.

My understanding is that the Maestro D' primarily uses Fingers In Every Pie in place of barter. If you look at the results, it's basically the same move as going to the market looking for something, except is substitutes Hot for barter spent. Since barter isn't any particular thing, yeah, you could roll to get 1-barter worth of stuff or a gun (worth 1-barter) etc. The downside is baked right into the move.

Personally, your Hardholder has two weapons here (plus any gear he's carrying), a gang and a bus. Either one can use the battle moves. Check the refbook pdf, harm rules pg 2.
When you’re behind the wheel, you can sucker someone, go aggro on them, or make a battle move, using your vehicle as a weapon. By extension, you can make those moves using a different weapon.

Now it sounds like what he really wants to do is Single Combat, not so much Seize By Force. If he wants to use the vehicle to inflict harm, they'll be using theirs to inflict harm back. If he wants to use his gang, the people inside the opposing vehicle will inflict harm back. The damage that's inflicted goes to When A Vehicle Suffers Harm (same page), which includes how much of the harm a vehicle takes will punch through to the people inside of it. Note this for the unarmored buggy:
Whether harm blows through to a vehicle’s driver and passengers, doesn’t blow through, or just hits them too without having to blow through, depends on the MC’s judgment of the circumstances and the vehicle.

That's the straight forward part. Now the interpretation part. It makes sense (seems real) to me that a large gang with shotguns can do more damage to a vehicle than one guy with a shotgun. It might make less sense that a small gang in a vehicle causes it to take less damage than just having one driver but since this isn't necessarily a blow-by-blow, combat rounds type thing, I'd probably go with it. So if there's more than a couple of guys in either vehicle, that's a small gang and modifies the damage based on the size of The Scorched.

Now if he wants to board instead, I wouldn't have that automatically ignore armor with the sedan. Think of Mad Max or Indiana Jones jumping onto a moving vehicle. They land on the roof or the truck bed or whatever and have to work to get inside. If they want to shoot through the window or something to ignore the vehicle, that's probably going to be Acting Under Fire to avoid getting thrown off. If an NPC pokes their head out to shoot the PC/his gang, they're a valid target. For the buggy, there's not much outside to be on. Once you're on, you can start shooting.

Has anyone had a chance to play The Show in a game yet? It strikes me as one of Vincent's "high mind-share" designs, kind of like the Battlebabe. It's got a lot of tools for causing trouble (battle truck, flame throwing guitar, a gang) but not all that many for getting out of it, pushing the world in a controlled way or even using any of those cool toys well. A Maestro D' might host or a Skinner might put on a performance, or a Gunlugger might be able to intimidate an entire gang into back down but The Show cracks open the world while standing at ground zero. Plus there's the push-pull dynamic of potentially being the leash-holder's meal ticket and the biggest drain on them at the same time. What have everyone's experiences been?

Here's a fairly specific example from my first few sessions in my very first AW game.
So Specialist Burke has just woken up from cryo-sleep to find Tammy Jackson has also been awoken but she's missing. Boom! My goal is to get Jax back. She's the only other person who can conceivably relate to what Burke is dealing with in this crazy, fucked-up world. With the help of a friendly Savvyhead (both of them talking through their respective Augury machines) he determines that Jax has been taken by a gang of about 8 thugs. So that's both fuckery and reward. "You know where Jax is. You know how to get to the local friendly-ish Hold. Do you want to try and play one man wrecking machine with a negative Hard and already wounded from coming out of cryo?"

Burke manages to make his way to the local Hold where the rest of the PCs are. The goal is still "rescue Jax". First, though, he needs medical attention, a silencer and a scope. With those, Burke figures he can snipe, since I had +3 Cool for Going Aggro. So now the goal is "find hi-tech gear", which is fairly close to your D&D-ish goals. That involved a bunch of chasing down leads, figuring out how Barter works, finding low quality crap (fuckery) and eventually someone who could make a silencer and someone else who would part with a scope (reward) but none of it involved the normal go to dungeon, kill things, take their stuff. It was just the people who lived in the Hold, their normal abilities, wants and problems. All of that culminated in running into a member of the gang that had Jax (fuckery) who was mostly just trying to do her thing and keep her head down. So now what, Burke? Take her hostage? Kill her in cold blood? You can't let her go because the whole damn Hold knows what you're planning and now so does she. Its not like there's a jail in town.

The sniper thing actually went down fine (reward) and most of the gang surrendered without being killed. One of them even wound up becoming an Ally due to advanced Hot, that's how long this took. So now she's alive but there's also half the gang who surrendered (fuckery). What now, Burke? You gonna put them on trial? How's that gonna work? The law is whatever the Holder says it is today. The police are his thugs. He said you can kill the gangers if you want. Oh, and by the way, the guy with the shiny rifle and invincible armor is now a local legend for dropping the gang single-handed. Oh, and he still never got medical attention because who has time for that shit?

So I got the rewards I was looking for (gear and rescuing Jax) and even some I didn't (the first Ally in the game, the gang's jeep) but Burke stirred up a ton of shit doing it. The Savvyhead wants a look at the Quarantine facility. Jax still has basically no understanding of how the world works while Burke has halfway gone native, she's more of a problem than a competent ally, the Hardholder and the Battlebabe both want Burke on their side but see each other and Burke as dangerous and potentially destabilizing. People are talking about these crazy ideas the new guy is spouting like "fair trial". There's now a power vacuum on the hold's northern flank and its only a matter of time before the crazy scientists of The Institute come looking for the Quarantine facility.