"Lettr finsh, d'maff."
"W-Well, of course not. We actually have a few options there, though: on the night prior to, or on the day of the attack, we could either sabotage the gate mechanisms with our own trappers- or a professional Engineer, if we can hire one- to prevent them from closing; we could bribe the guards on duty, or plant our own men in the Watch; or, if we get our hands on some gunpowder, we may be able to destroy one or more of them entirely.
Ideally, we would have three of the city's four main entrances compromised, but we technically only need one."
She paused for a moment to take a swig from a flask on her belt.
"Anyway, remember that only half of our forces will need to infiltrate the city; the rest of our men will remain concealed in two groups outside, on opposite sides of the city, awaiting an agreed-upon signal. Once everything's prepared and the inside group gives the signal, the outside groups will charge the gates and create a diversion- when the guards realize they can't shut them out, they'll have to pull troops from the rest of the city to the walls, and when that happens, our inside group will break cover and take the market by storm.
Once the city center's been... suitably ravaged, and everything we can packed on the wagons, the inside group will head out the third gate, if available, or flank the guards at one of the other two. We... don't actually know what sort of military presence the city has, but we should be able to surprise and divide them enough to make a clean getaway- especially if we can poison them or eliminate key figures prior to the attack. Needless to say, there are many elements that could be added that aren't strictly necessary, but the more that fall into place, the easier the operation will go... and we only get one shot either way, so we'll have to make sure we've stacked every odd we can in our favor."