Bimonotone subdivisions in two dimensions are subdivisions all of whose sides are either vertical or have nonnegative slope. They correspond to statistical estimates of probability distributions of strongly positively dependent random variables. The number of bimonotone subdivisions compared to the total number of subdivisions of a point configuration provides insight into how often the random variables are positively dependent. We give recursions as well as formulas for the numbers of bimonotone and total subdivisions of $2\times n$ grid configurations in the plane. Furthermore, we connect the former to the large Schröder numbers. We also show that the numbers of bimonotone and total subdivisions of a $2\times n$ grid are asymptotically equal. We then provide algorithms for counting bimonotone subdivisions for any $m \times n$ grid. Finally, we prove that all bimonotone triangulations of an $m \times n$ grid are connected by flips. This gives rise to an algorithm for counting the number of bimonotone (and total) triangulations of an $m\times n$ grid.