Placement of window AC in open living space
I would probably use window 12 over number 1 because that is where the heat load is and the room is larger. 
3 or 5 are both good options but I would use 3 because of  the proximity for the discharge to blow towards the family room.
If this were my place I would install mini splits , last week I saw an advertisement for a top brand 12k btu mini split with a 10 year warranty for 475.00 installed, I am sure that means you have to put the power in but hanging a split and mounting the outside unit on a plastic pad can be done very quickly, there are even some full DIY options out there but they are more expensive. 
The split units can be mounted above windows or on walls and can add value to your home including providing a efficient heat source in the winter