All right, replying in post order here so forgive me if I cover something y'all have already discussed.
rednblackI've got no preference on medevac'ing the doc; that's your call

Leadership is indeed an initiative pass thing; however, you all do have access to various combat maneuvers that could apply here. Just because you're on foot doesn't mean you can't execute an overwatch manevuer, or even a diamond formation; that's partly what drones are for after all.
Applicable maneuvers in this case are as follows.
Diamond formation, but only if you can provide forward, rear, and side firing arcs while embarked
Traveling Overwatch, especially with Wires and the Humvee acting as one member with August or Weedy acting as a second
As for the benefits of Leadership, page 49 details the teamwork tests the hits act as. Essentially, the person you're directing receives a +1 to his or her Limit and a dice pool bonus equal to your hits, limited by the skill of the character being assisted. So, you got 6 hits; if Weedy or Gale had a Perception skill of 6 they could keep all 6 hits; if not they'd get to keep as many hits as they had skill ratings for. Now, as mentioned above Leadership is an instant thing, not a persistent thing, so no go on your attempt to use it on both Weedy and Gale at the same time for an extended duration.
KoshnekChuck knows that all but one of the buildings August has pointed out are structurally sound; that leaves three buildings which are not only structurally sound but could work as shelter. Unfortunately, you can't tell from the outside if the structure has been reinforced in some way or another.
No retconning gear at this time, Koshnek, sorry. I asked for gear loadouts for a reason

The Termite shaman, as far as y'all know, is rumoured to be hiding out on the east bank of the South Branch Chicago River, somewhere between W Cermak Rd to the north and W24th Pl to the south. There are four buildings on the riverbank between those streets, three of which are still structurally sound according to Chuck's demo knowledge.
RavensoracleI'll be making some Pilot rolls for the drones to see if they manage to follow your plans; dogbrains may or may not be good at following orders. So, go ahead and roll a Navigation test; each hit will get added as a standard teamwork test to the Pilots Maneuvering roll.
rednblackI was talking about the Humvee in terms of handling issues; the Banshee just doesn't have much room for more drones.
You could try to evac on the Humvee with Viper team, Dr. Clay, and all the BS mercs, but you'd be at potential a -5 (or more) to Handling at that point, and some of you or the BS mercs might have to hang on for dear life on the outside of the vehicle (essentially standing on the footboards and holding on to the roof rails.
The Banshee has room for everyone if some stays inside the Humvee; Banshee has 12 seating capacity, 6 of which are used for the Humvee. That leaves 6 for you all and your gear and medevac drone, which means it's a tight fit already. However, the Humvee and Medevac drone does have room for occupants, so Dr. Clay and the mercs could hitch a ride inside the vehicles without any issue.
Clearer?
All right, landing post coming up; Wires managed to execute the landing perfectly, and as sneakily as the elements and equipment allows

EDIT:
RavensoracleI need a plan for where the various Fly-Spies are going. You're all currently in a Noise 2 environment; I hope everyone remembered to bring datajacks or similar
Blazrath, ReyjinnYou both instantly know this is an area that's seen some shit, and it's probably going to get worse. The current Background Count is 2, and is aspected towards Death. Any skill test that involves a magical ability (yes, that means Longarms for you, Blazrath) is at a -2 penalty. The rating of any active foci, sustained/quickened spells, and rituals are similarly reduced by 2. Sucks to be a magician in the CZ, chummers...
BlazrathI just noticed your Adept Powers are a little mismatched in your Chummer sheet; you've got 4 Power Points but 5.5 PP worth of powers; I'm guessing you just forgot to remove Improved Reflexes 1, since you have Improved Reflexes 2 as well?
EveryoneAt the time of disembarkation your various Geiger sensors blip occasionally, enough to indicate that there's no radiation present beyond the usual cosmic background radiation.
The route to 26th and State is right around 2km, which will take you about 10 minutes if you move at the fastest pace you can while remaining stealthy and keeping a solid lookout. Anything faster than 10m/CT (which is around 12km/h, or 200m/min) is going to mean Sneaking and Navigation tests that will suffer from negative penalties.
Have fun
