New custom move for transient PCs

So far my players have chosen playbooks that don't include explicit built-in motivations or NPC relationships, i.e., no hardholder, hocus, operator, or chopper. They basically freelance smuggling and escort gigs up and down a river valley dotted with hardholds. Since I don't want to come up with all the NPC relationships alone, I made this custom move:

When you roll up to a new hardhold, you know someone there. Describe the relationship to the MC and roll+hot. On a 10+ both, on a 7-9 choose 1:
*they're not pissed at you
*you don't owe them a favor

What am I failing to account for with this move?

It's not clear to me what 'new' means -- is that in the fiction, or in the game? Move triggers should be fictional if at all possible, but is this move meant to represent the PCs just knowing so many people that even when they go somewhere they've never been, they happen to know someone there? Or is it intended to be for hardholds they have visited previously (in the fictional past, but not in the actual-game=time), and therefore know someone there because of that?

If the latter, a change to something like 'when you visit a hardhold you haven't been to in awhile' might be clearer, or you could make it a straight-up meta-move I guess (some do exist, but they're mostly beginning-of-session moves.)

Because, I mean, you can achieve the 'I don't want to do all the work' part of this move by just asking questions as the MC. "Okay so you're pulling up to The Plaza and you spot someone you know -- who is it, and why do you owe them a favour?"

If the goal is to automatically generate situations with more obvious teeth, then the move is better for that, because they could miss the roll and because the 7-9 choices give you a soft move for free -- but what happens when all your PCs visit a new hardhold together, for some other important reason, and now suddenly you have 4 new NPCs, two of whom are pissed off, and one missed roll? It could get cluttered (though it shouldn't be hard to tie those NPCs in to whatever the initial situation is.) Whereas just asking questions allows you to get as much or as little help as you need.

Thanks! This is really helping me hone in on it. You make good arguments for just asking questions. My group is used to more traditional RPGs and this move is conceived to help them ease into those kinds of loaded questions where I just declare something about their character and ask them for details. I suppose this is one way to disclaim decision making.

Meanwhile, here's a refinement:

When you roll up to a hardhold you haven't been to in awhile, someone is looking for you. Tell the MC who it is and roll+Hot. On a 10+ both. On a 7-9 choose one:
*they aren't pissed at you
*you don't owe them anything

In cases you mention where all of them make a roll and risk detracting from why they're there, I'll remind them that the person looking for them could be the person they came to deal with. (On a miss, you can bet it's the person they're coming to deal with, and he's pissed and they probably owe him.) If they all make up someone new, well I'll just have a snarling bundle of new cues to work into the scene.

It's a little more work, but it might be fun to use what you have as a framework for character-specific custom love letters.  Switch up the pick list and maybe even the stat.  You can also have them point to E.g., an Angel might have roll+Sharp, and pick from:

* You've heard this hold does a good business in medical supplies.  If you go looking to restock, you get twice what you pay for.
* Unfortunately, the reason there's so much supply around is that nobody knows how to use it right, and everybody's *really* excited the hold has a new Angel.

Ooh, yes. Love letters would be the perfect way to limit this from getting out of hand... Good call.

Mid-session love letters? Or, I guess if the likely pacing is that PCs will arrive at new hardholders between sessions, that could definitely be a useful way to introduce a bunch of situation all at once.

Though I'd be worried that if that became the regular pacing, it would start to feel more like a serial adventure (what problems does this Hardhold have? Let us deal with/exploit them and then move on to the next one!)

Hmm.. mid-session love letters could be interesting. I could hand one out when triggered by in-fiction cues or at the tail end of a bathroom break. I could choose which player gets it and spread them out over time. I could refrain from handing one out. I could tailor them- say, to a specific PC or even fictional cue, like, Someone at The Plaza is looking for you. Tell the MC...

It's almost like a custom move that starts with, When the MC feels like it...

Might be too far down the rabbit hole, though.

Mid-session love letters? Or, I guess if the likely pacing is that PCs will arrive at new hardholders between sessions, that could definitely be a useful way to introduce a bunch of situation all at once.

Though I'd be worried that if that became the regular pacing, it would start to feel more like a serial adventure (what problems does this Hardhold have? Let us deal with/exploit them and then move on to the next one!)

I'd actually really like a good serial structure for a *-world game, but that's neither here nor there. :)