[Zubersoft]

Go into the annotation settings and enable "Combine freeform annotations". Is there a reason you unchecked that setting? That will group all of the drawings into one annotation which you can then move all at once, instead of having to move each individual stroke as a separate annotation. I added that option in case there were some users who prefered not to have that automatic grouping, but as you can see, it makes managing the annotation much more difficult. 

Also, be aware that in order to drag a freeform drawing, you need to press on one of the strokes and drag it. Pressing inside the bounding box but not on a stroke will result in the annotation being deselected, because you didn't technically tap directly on it. It's implemented this way because otherwise it would be impossible to work with annotations that are all close to each other.

Mike