Resky,
I have flown all three airplanes in that picture, in all manner of flight. I'm certainly not an aeronautical engineer, but I can say without a doubt that the only thing that Bird Dog did better than the other two, was sky write, and ferry fast and comfortable. Workwise the cubs will tow an identical load faster (IMHO that means more efficient flying) and slower (again in my mind more efficient flying) Bear in mind that they are accomplishing all that with two less cylinders and a fixed pitch vs. the 88" Mac. The reason I pointed out the AOA is because
it is struggling to do what the others are doing... it actually would have flown without flaps, but with an even greater penalty on the AOA
To address the flap question, You can get by towing without flaps in the bird dog, but not in formation with cubs for very long. Hauling say 3500 square feet of sign in a cub you can just blip the throttle when it settles some, and it will start flying again. The BD doesn't have the wing to let it get that slow, and relying on power alone takes too long...It is also not conducive to good cooling as the nose starts getting a little too high... They make a good glider tug, but you tow gliders quite a bit faster than banners.
I would have to look up the weight on the C-305, But I want to say it was in the low 1600s not a porker, but not exactly a featherweight either.
Again, I actually love the Bird Dog, but since the original question pitted it up against the cub in the back country.... Well..sorry IMHO it just ain't happening... And again IMHO (which doesn't account for much) A good, light 180 is probably going to be a better bet by a good amount.
Of course all of this also depends on your interpretation of back country
I think Back country wise it is probably similar performance wise to a Scout, but using more horsepower to accomplish the same results. <~~~ that oughta get the natives all up in arms
Take care, Rob