We investigate stabilizing and eschewing factors on bistability in polar-orthotropic shells in order to enhance morphing structures. The material law causes stress singularities when the circumferential stiffness is smaller than the radial stiffness (β < 1), requiring a careful choice of the trial functions in our Ritz approach, which employs a higher-order geometrically nonlinear analytical model. Bistability is found to strongly depend on the orthotropic ratio, β, and the in-plane support conditions. An investigation of their interaction offers a new perspective on the effect of the hoop stiffness on bistability: while usually perceived as promoting, it is shown to be only stabilizing insofar as it prevents radial expansions; however, if in-plane supports are present, it becomes a redundant feature. Closed-form approximations of the bistable threshold are then provided by single-curvature-term approaches. For significantly stiffer values of the radial stiffness, a strong coupling of the orthotropic ratio and the support conditions is revealed: while roller-supported shells are monostable, fixed-pinned ones are most disposed to stable inversions; insight is given by comparing to a simplified beam model. Eventually, we show that cutting a central hole is a suitable method to deal with stress singularities: while fixed-pinned shells are barely affected by a hole, the presence of a hole strongly favours bistable inversions in roller-supported shells.