The simplest way to do the original problem is to say that the area of a small ring, of inner radius r and thickness dr is approximately [itex]2\pi r[/itex], the length of the ring, times dr, the thickness. That would be exactly correct if it were a rectangle of length [itex]2\pi r[/itex] and width dr. The point is that in the limit, as we change from Riemann sum to integral, that "approximation" becomes exact (the "[itex]dr^2[/itex] in your and Dick's reasoning) goes to 0 : the area is given by [itex]\int \pi r dr[/itex].
Can someone explain to my why this is a physics problem and not a mathematics problem?