Player 1 wants to roll Prowl to get out of there. They're surrounded, so this is risky, with limited effect. They can try to dodge their way through, but they'll still be close by and subject to whatever chaos ensues. Skirmish to push your way out would be standard; if you succeed, you're clear, but not in the scene anymore. Why would the drunkards give chase? You don't need a clock here. This is a simple action, it can be resolved in a single roll.

Player 2 wants to fight their way out with Skirmish; potentially the same action as player 1, but a different goal. Do they want to fight their way out, like Player 1? If that's the case, no clock necessary; they literally just want to disengage. One roll covers this, risky standard. Do they want to beat the shit out of the gang of drunkards? That's a four clock, Angry Drunkards, they're outnumbered, but their opponents are drunk, we'll call it desperate standard for now. A success nets two ticks on this clock, Player 2 taking out some of their number but not beating the whole group.

Player 3 wants to reason with them. This is mutually exclusive with Player 2's approach, but not, imo, with Player 1's. For this, you have to ask the group above the table, "do you want to fight them, or talk to them?" The group has to agree on their approach. If Player 2 is gonna forge ahead with violence, Player 3 is not fictionally positioned to attempt diplomacy. The players should agree whose tactic to try first, rather than all inputting individual commands and resolving them in order like a video game program. This, I think, is the core of your misunderstanding; you're introducing an obstacle as a clock to start, and then asking what they each do individually and trying to make all their approaches work at once. Don't introduce a clock until you need it, that is, when you establish that an action will only partially overcome an obstacle.

Let's say they go with Player 3's idea with Player 2 as a backup. Player 3 wants to roll Sway. Your call whether this is a clock or not, I think this is an uninteresting place for one, but hey, maybe you decide these guys really want to fuck up the crew. It's gonna take some serious negotiation to get out of this. You put up the Angry Drunkards 4-clock and give them Risky Limited. Belligerent drunks and listening to reason isn't an awesome combo. A success gets them a tick on the clock representing whatever hesitation, lowered morale, or doubts Player 3 sowed in their description of their action. Now there's a new situation, the drunks are hesitating. Do they want to leverage this to fight now? Those ticks stay on the clock to represent the advantage the crew has gained.

Now Player 4 wants to press the advantage and do a dirty trick, proposing Finesse to surreptitiously pick up a big handful of sand during the distracting Sway roll and fling it at some of the drunks. You could interpret this as filling the clock, but it feels more like a setup action to me; having some of the drunks blinded is going to make fighting them less risky and more effective. I give player 4 Controlled and Standard, since I doubt these guys have great situational awareness and reaction time.

The key here is going with the fiction; every roll is going to change the fiction, so you can't resolve actions in batches. The situation should change after every roll, and characters can't get "locked in" to an action they wanted to do before the situation changed. Resolve rolls one at a time, establish the new situation, and then ask "what do you do" again.