In my calculus book (Stewart), the theorem is proved for a simple region (I understand that this is being enclosed by a simple curve). But then it is specified that the theorem can be extended for a finite union of simple regions that do not overlap, and even for regions that are not simply connected (that is, with holes).
So it doesn't occur to me about what kind of region the theorem might not apply to.
Green's theorem works only for the case where C is a simple closed curve. If C is an open curve, please don't even think about using Green's theorem.
So what is a simple curve? A curve that does not cross itself. So if the region is a finite union of simple regions that overlaps, the curves that enclose the region will not be simple as they will cross each other. So Green's theorem is not applicable there.
Now comes the question. When can we use Green's theorem?