You will learn shortcuts to setting it up. Experience counts. A pain to set up? Not for me.
Will it blow over in a strong wind? Yes it will. How many windy days do you have? Just use the retired gun feature on non windy days. I'm not trying to "open a can of worms" here, but you have probably noticed that it is not a perfect world. I've seen a few wingers blow over with enough wind.
You can also make a couple of U shaped stakes, with one side longer than the other, and place the U shaped end over the opposite corners of the BB base, and drive it into the ground. That will hold it.